1-Chloroethyl chloroformate → HCID 68019354, compound

HRID 456257Notes

Reaction equation

HRID 456257 reaction equation
C([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:10]([N:31]([CH3:56])[CH2:32][CH2:33][NH:34][C:35](=[O:55])[C@H:36]([CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:37][C:38]([O:40][CH3:41])=[O:39])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[CH3:41][O:40][C:38]([NH:37][C@H:36]([C:35]([NH:34][CH2:33][CH2:32][N:31]([CH3:56])[C@H:10]1[C@H:11]([N:13]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[S:14]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][NH:8][CH2:9]1)=[O:55])[CH:42]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:39]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 70197038HCID 70197038, compound

Product 1

HCID 68019354HCID 68019354, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-(2-{[(3R,4R)-1-benzyl-4-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}pyrrolidin-3-yl](methyl)amino}ethyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (168 mg, 0.15 mmol), 1-chloroethyl chloroformate (72 mg, 0.5 mmol) in 1.5 mL of 1,2-dichloroethane was stirred overnight at reflux. The solvent was evaporated, the residue was re-dissolved in MeOH and the mixture was refluxed for 1 hour. MeOH was evaporated and the residue containing compound the deprotected pyrrolidine was used for the next step without additional purification. LC-MS APCI: m/z 695.3 [M+H]+.

Workup

  1. temperatureat reflux
  2. customThe solvent was evaporated
  3. dissolutionthe residue was re-dissolved in MeOH
  4. temperaturethe mixture was refluxed for 1 hour
  5. customMeOH was evaporated
  6. additionthe residue containing compound the deprotected pyrrolidine
  7. customwas used for the next step without additional purification

Sources & evidence

ORD record
ord-d511138c48bf4f9eaf6a47c52999f6bd
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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