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Chemical Structure| 142356-33-0 Chemical Structure| 142356-33-0
Chemical Structure| 142356-33-0

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Boc-NH-C6-Br is a cleavable linker used for antibody-drug conjugates (ADC).

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Product Details of Boc-NH-C6-Br

CAS No. :142356-33-0
Formula : C11H22BrNO2
M.W : 280.20
SMILES Code : CC(C)(C)OC(=O)NCCCCCCBr
MDL No. :MFCD06201019
InChI Key :NXQXVXILNVTMNA-UHFFFAOYSA-N
Pubchem ID :16211353

Safety of Boc-NH-C6-Br

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H318-H411
Precautionary Statements:P273-P280-P305+P351+P338-P310-P391-P501
Class:9
UN#:3082
Packing Group:

Application In Synthesis of Boc-NH-C6-Br

* 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.

  • Downstream synthetic route of [ 142356-33-0 ]

[ 142356-33-0 ] Synthesis Path-Downstream   1~1

  • 1
  • tert-butyl 6-bromohexylcarbamate, cesium carbonate [ No CAS ]
  • [ 1191909-21-3 ]
  • [ 1191909-22-4 ]
  • [ 142356-33-0 ]
  • [ 939-69-5 ]
  • 4-(6-(2-cyano-7-nitrobenzo[d]thiazol-6-yloxy)hexylcarbamoyl)-2-(3-(dimethylamino)-6-(dimethyliminio)-6H-xanthen-9-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; trifluoroacetic acid; In diethyl ether; n-heptane; dichloromethane; diethylene glycol dimethyl ether; ZrO(NO3)2*H2O; ethyl acetate; methoxybenzene; acetone; Part D. Synthesis of 4-(6-(2-cyano-7-nitrobenzo[d]thiazol-6-yloxy)hexylcarbamoyl)-2-(3-(dimethylamino)-6-(dimethyliminio)-6H-xanthen-9-yl)benzoate (compound 3087) 6-Hydroxybenzo[d]thiazole-2-carbonitrile (352 mg) was heated in a microwave with ZrO(NO3)2*H2O (462 mg) and acetone (7 mL) at 100° C. (200W) for 10 min. Product was extracted with dichloromethane and eluted through silica with heptane:ethyl acetate (1:1). Yield 222 mg. 6-Hydroxy-7-nitrobenzo[d]thiazole-2-carbonitrile (100 mg) was heated to 70° C. at 50W for 30 minutes in a microwave with acetone (2 mL), potassium carbonate (125 mg), and tert-butyl 6-bromohexylcarbamate (139 mg). After which an additional 150 muL tert-butyl 6-bromohexylcarbamate was added and reaction was heated to 80° C., 75W, for 30 minutes. After which an additional 300 muL tert-butyl 6-bromohexylcarbamate, cesium carbonate (162 mg) and diglyme (1 mL) was added and reaction was heated to 100° C., 75W, for 250 minutes. The reaction was partitioned between ethyl acetate and bicarbonate, washed with aqueous citric acid and brine, and evaporated. The crude material eluted through a silica column with a mixture of heptane: ethyl acetate (2:1). Yield 44percent tert-Butyl 6-(2-cyano-7-nitrobenzo[d]thiazol-6-yloxy)hexylcarbamate (50 mg) was added to cold (0° C.) solution of dichloromethane (1 mL), trifluoroacetic acid (1 mL), and anisole (99 muL). After 30 minutes, the majority of solvent was evaporated, and 30 mL of diethyl ether was added. The precipitate was isolated and used without further purification.
 

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