Dimethylformamide → HCID 31934446, compound

HRID 2269628Notes

Reaction equation

HRID 2269628 reaction equation
CN(C=O)C.[NH:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:7]([C:15]([OH:17])=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC(OCC(C)C)=O.[CH2:33]([NH2:37])[CH:34]([CH3:36])[CH3:35]>C(N(CC)CC)C>[NH:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:7]([C:15]([NH:37][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6558IsobutylamineHCID 62365Isobutyl chloroformateHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 31934446HCID 31934446, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a DMF solution containing a mixed anhydride prepared from 2.0 g of Boc-Phe-OH, 1.15 ml of triethylamine and 1.08 ml of isobutyl chloroformate, 1.50 ml of isobutylamine was added under ice cooling and the resultant mixture was stirred for 14 hr. The reaction mixture was treated similarly to that in Example 51 (Process 1) to give 1.91 g of the title compound.

Workup

  1. additionwas added under ice cooling
  2. additionThe reaction mixture was treated similarly to that in Example 51 (Process 1)

Sources & evidence

ORD record
ord-f71e0497358e45808892d8a8874d3d7d
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

Loading…