tert-Butanol → HCID 54344896, compound

HRID 1419723Notes

Reaction equation

HRID 1419723 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17](=[O:25])[C@@H:16]1[CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:49](O)([CH3:52])([CH3:51])[CH3:50].CCN=C=NCCCN(C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:49]([O:23][C:22](=[O:24])[CH2:21][N:18]1[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:40][C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[C@@H:16]([CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C:17]1=[O:25])([CH3:52])([CH3:51])[CH3:50]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 54425150HCID 54425150, compound

Product 1

HCID 54344896HCID 54344896, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane were dissolved 1.7 g of (S,S)-4-[2-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionyl]-3-(3-benzyloxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid produced in Reference Example 34, 2 ml of tert-butanol and 1.6 g of 4-dimethylaminopyridine. To the solution was then added 0.6 g of WSC, and the mixture was stirred for 24 hours at room temperature. Dichloromethane was distilled off, and the residue was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous saline solution, which was then dried (Na2SO4), followed by concentration under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (AcOEt), followed by crystallization from ether/hexane to afford 1.02 g of the title compound as colorless crystals.

Workup

  1. distillationDichloromethane was distilled off
  2. extractionthe residue was subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous saline solution, which was then dried (Na2SO4)
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe concentrate was purified by means of a silica gel column chromatography (AcOEt)
  7. customfollowed by crystallization from ether/hexane

Sources & evidence

ORD record
ord-d47b4934dec24ea5a0dbe5ba5ba7336b
Source dataset
uspto-grants-1999_03
Patent number
US05888531

Reaction notes

Loading…