[ CAS No. 927679-54-7 ] {[proInfo.proName]}

Name: 927679-54-7|rel-(1R,5S,6r)-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid|95%
Brand: Ambeed
SKU: A124863
Price: 772.0 USD
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Quality Control of [ 927679-54-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 927679-54-7 ]

SDS Specification

Alternatived Products of [ 927679-54-7 ]

Product Details of [ 927679-54-7 ]

CAS No. :	927679-54-7	MDL No. :	MFCD12198680
Formula :	C₁₁H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GYEQQDCMLKKYGG-DHBOJHSNSA-N
M.W :	227.26	Pubchem ID :	39871576
Synonyms :

Safety of [ 927679-54-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 927679-54-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 927679-54-7 ]
Downstream synthetic route of [ 927679-54-7 ]

[ 927679-54-7 ] Synthesis Path-Upstream 1~12

1
[ 927679-54-7 ]
[ 419572-18-2 ]

Reference： [1] Patent: WO2014/81718, 2014, A1, . Location in patent: Page/Page column 118

2
[ 134575-37-4 ]
[ 927679-54-7 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	Stage #1: With sodium hydroxide In ethanol at 0 - 20℃; for 3 h; Stage #2: With hydrogenchloride In water	The tert-butyl 6-ethoxycarbonyl-3-azabicyclo[3.1.0]hexane-3-carboxylate exo-isomer (613 mg, 2.40 mmol) prepared in Example 2 was dissolved in 6 mL of ethanol and 2N NaOH (2.40 mL, 4.80 mmol) was added dropwise at 0° C. After stirring at room temperature for 3 hours, the completion of the reaction was confirmed by TLC (hexane:ethyl acetate=6:1). After the reaction was completed, the reaction mixture was concentrated under reduced pressure and then extracted by adding methylene chloride and water. After removing the organic layer containing byproducts, the aqueous layer was acidified with 1N HCl and extracted with methylene chloride. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 527 mg (96.5percent) of the target compound. ¹H NMR (300 MHz, CDCl₃) δ 3.74 (d, J=11.1 Hz, 1H), 3.66 (d, J=11.3 Hz, 1H), 3.53-3.45 (m, 2H), 2.17 (br, 2H), 1.55-1.53 (m, 1H), 1.48 (s, 9H).

Reference： [1] Patent: US2014/343295, 2014, A1, . Location in patent: Paragraph 0087; 0088; 0089
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 4, p. 1067 - 1070

3
[ 419572-18-2 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

4
[ 187681-87-4 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

5
[ 1366657-90-0 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

6
[ 134575-05-6 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

7
[ 705-35-1 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

8
[ 13949-99-0 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

9
[ 134575-13-6 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

10
[ 134575-07-8 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

11
[ 134575-06-7 ]
[ 927679-54-7 ]

Reference： [1] Org. Process Res. Dev., 2011, vol. 15, # 5, p. 1052 - 1062

12
[ 24424-99-5 ]
[ 927679-54-7 ]

Reference： [1] Patent: US2014/343295, 2014, A1,

[ 927679-54-7 ] Synthesis Path-Downstream 1~88

1
[ 419572-18-2 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

2
[ 187681-87-4 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

3
[ 1366657-90-0 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

4
[ 927679-54-7 ]
[ 1173177-23-5 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

5
[ 927679-54-7 ]
[ 1173239-42-3 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

6
[ 927679-54-7 ]
[ 1173239-39-8 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

7
[ 927679-54-7 ]
[ 72235-56-4 ]
[ 1173177-20-2 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

8
[ 134575-05-6 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

9
[ 705-35-1 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

10
[ 13949-99-0 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

11
[ 134575-13-6 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

12
[ 134575-07-8 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

13
[ 134575-06-7 ]
[ 927679-54-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1052 - 1062

14
[ 927679-54-7 ]
[ 1269429-71-1 ]

Yield	Reaction Conditions	Operation in experiment
75%		INTERMEDIATE 13fert-butyl (lj¾, 5ff, 6r)-6-( 1,3 i14-oxadiazol-2-yl)-3-azabicyclo [3.1.0] hexane-3-carboxylate (i-13)Step A: /gr/-butyl ( IR. 5S, 6/)-6-(hydrazinocarbonyl)-3-azabicyclo [3.1.0] hexane-3-carboxylate; HBetaomicronomicronNu^ "OmicronNuEtaNu¾To a solution of 4.50 g (19.8 mmol) (IR, 5S, 6r)-3-(tert-butoxycarbonyl)-3- azabicyclo [3.1.0] hexane-6-carboxylic acid in 50 ml anhydrous tetrahydrofuran at -10C was added 3.04 ml (21.8 mmol) triethylamine followed by 2.08 ml (21.8 mmol) ethyl chloroformate slowly. The reaction was stirred between -20C to -10C for 20 min. The solid was filtered off and rinsed with tetrahydrofuran. The tetrahydrofuran filtrate was added into 1.04 ml (33.4 mmol) hydrazine hydrate in 50 ml anhydrous methanol at 0C. The reaction was stirred at ambient temperature for 2 h. The crude product was concentrated and purified by using a Biotage Horizon system (0-10% ethyl acetate/methanol with 10% ammonia) to give 3.0 g (75%) of the title compound as white solid. 1H NMR (CDC13): delta 3.67 (d, J = 1 1.2 Hz, 1H), delta 3.65 (d, J - 10.8 Hz, 1H), delta 3.42 (d, J = 10.7 Hz, 2H), delta 2.09 (s, 2H), 6 1.43 (s, 9H)5 delta 1.31 (m,lH).

Reference： [1]Patent: WO2012/12314,2012,A1 .Location in patent: Page/Page column 55

15
[ 927679-54-7 ]
[ 1269429-70-0 ]

Reference： [1]Patent: WO2012/12314,2012,A1

16
[ 927679-54-7 ]
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]ctane-2-carbohydrazide [ No CAS ]
C₂₅H₃₃N₅O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	Example 47: Synthesis of (2S,5R)-2-(5-(3-az.abicyclof3.1.0]hexan-6-yl)-l,3A-oxadiazol-2- -7-oxo-l ,6-diaz.abicyclol 3.2.1 loctan-6-yl hydrogen sulfate (Compound 740) ESI-MS (Epsilon , m/z): 372.3.

Reference： [1]Patent: WO2013/149121,2013,A1 .Location in patent: Page/Page column 123

17
[ 927679-54-7 ]
C₂₅H₃₁N₅O₅ [ No CAS ]

Reference： [1]Patent: WO2013/149121,2013,A1

18
[ 927679-54-7 ]
C₁₈H₂₅N₅O₅ [ No CAS ]

Reference： [1]Patent: WO2013/149121,2013,A1

19
[ 134575-37-4 ]
[ 927679-54-7 ]

Yield	Reaction Conditions	Operation in experiment
96.5%		The tert-butyl 6-ethoxycarbonyl-3-azabicyclo[3.1.0]hexane-3-carboxylate exo-isomer (613 mg, 2.40 mmol) prepared in Example 2 was dissolved in 6 mL of ethanol and 2N NaOH (2.40 mL, 4.80 mmol) was added dropwise at 0 C. After stirring at room temperature for 3 hours, the completion of the reaction was confirmed by TLC (hexane:ethyl acetate=6:1). After the reaction was completed, the reaction mixture was concentrated under reduced pressure and then extracted by adding methylene chloride and water. After removing the organic layer containing byproducts, the aqueous layer was acidified with 1N HCl and extracted with methylene chloride. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 527 mg (96.5%) of the target compound. 1H NMR (300 MHz, CDCl3) delta 3.74 (d, J=11.1 Hz, 1H), 3.66 (d, J=11.3 Hz, 1H), 3.53-3.45 (m, 2H), 2.17 (br, 2H), 1.55-1.53 (m, 1H), 1.48 (s, 9H).

Reference： [1]Patent: US2014/343295,2014,A1 .Location in patent: Paragraph 0087; 0088; 0089
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1067 - 1070

20
[ 927679-54-7 ]
[ 1564262-56-1 ]