Tetrahydrofuran → HCID 178456001, compound

HRID 1655722Notes

Reaction equation

HRID 1655722 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:46])[CH:20]([NH:27][C:28](=[O:45])[C@H:29]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[NH:30][C:31](=[O:37])[C@H]2CCCN2)[CH2:21][C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH2:12][CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:47](Cl)(=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49].C([N:56]([CH2:59][CH3:60])[CH2:57][CH3:58])C.O1CCC[CH2:62]1>>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:46])[C@@H:20]([NH:27][C:28](=[O:45])[C@@H:29]([NH:30][C:31]([C@H:59]2[CH2:60][CH2:62][CH2:58][CH2:57][N:56]2[C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])=[O:37])[CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:21][C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH2:12][CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 178455993HCID 178455993, compound

Product 1

HCID 178456001HCID 178456001, compound

Procedure

A mixture of 95 mg (0.133 mmol) of N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]-α-[(3-phenyl-N-D-prolyl-L-alanyl)amino]imidazole-4-propionamide, 0.025 ml (0.199 mmol) of pivaloyl chloride and 0.185 ml (1.33 mmol) of triethylamine in 10 ml of tetrahydrofuran was stirred at room temperature overnight. After the usual working-up and chromatographic purification on silica gel with a 20:1:0.1 mixture of methylene chloride, methanol and ammonia, there was obtained (S)-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]-α-[(S)-α-[(R)-1-pivaloyl-2-piperidinecarboxamido]hydrocinnamamido]-imidazole-4-propionamide as a thin-layer chromatographically uniform solid, MS: 722 (M+H)+.

Workup

  1. customchromatographic purification on silica gel
  2. additionwith a 20:1:0.1 mixture of methylene chloride, methanol and ammonia

Sources & evidence

ORD record
ord-454673d4a0d6498bbbe115470f303b00
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

Loading…