Ammonia → HCID 178456006, compound

HRID 1655742Notes

Reaction equation

HRID 1655742 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19]([C@@H:21]([NH:28][C:29]([C@H:31]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:32][C:33]([O:35]CC)=O)=[O:30])[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)=[O:20])[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:45]>CO>[C:33]([CH2:32][C@@H:31]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:29]([NH:28][C@@H:21]([CH2:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1)[C:19]([NH:18][C@@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C@@H:9]([OH:17])[CH2:10][C@@H:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=[CH2:13])=[O:20])=[O:30])(=[O:35])[NH2:45]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178456017HCID 178456017, compound

Product 1

HCID 178456006HCID 178456006, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 100 mg of ethyl (R)-3-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]-4-phenylbutyrate in 30 ml of methanol was saturated with ammonia for 1-2 minutes and subsequently left to stand at room temperature for 12 hours. Thereafter, the solvent was removed under reduced pressure and the residue was chromatographed on silica gel with 10% methanol in methylene chloride as the eluting agent, to obtain 63 mg (66%) of (S)-α-[(R)-α-(carbamoylmethyl)hydrocinnam-amido]-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide as a resin. MS: 580 (M+H)+.

Workup

  1. waitsubsequently left
  2. customThereafter, the solvent was removed under reduced pressure
  3. customthe residue was chromatographed on silica gel with 10% methanol in methylene chloride as the eluting agent

Sources & evidence

ORD record
ord-008df9bb123e48d886665d0b546999ab
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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