Dimethylamine → HCID 178456015, compound

HRID 1655745Notes

Reaction equation

HRID 1655745 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](OCC)=[O:34])=[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.[CH3:45][NH:46][CH3:47]>>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:20])[C@@H:21]([NH:28][C:29](=[O:30])[C@@H:31]([CH2:32][C:33](=[O:34])[N:46]([CH3:47])[CH3:45])[CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:22][C:23]2[N:24]=[CH:25][NH:26][CH:27]=2)[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

Participants

3

Reactant 2

HCID 674DimethylamineHCID 178456017HCID 178456017, compound

Product 1

HCID 178456015HCID 178456015, compoundYield 20%

Procedure

80 mg (0.13 mmol) 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 were taken up in 2 ml of a 5.6 molar alcoholic dimethylamine solution and heated to reflux for 3 hours. The solution was then evaporated and the residue was chromatographed on silica gel with a 20:1 mixture of methylene chloride and methanol to obtain 33 mg (20%) of (S)-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]-α-[(R)-α-[(dimethylcarbamoyl) methyl]hydrocinnamamido]imidazole-4-propionamide as an amorphous powder. MS: 608 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe solution was then evaporated
  4. customthe residue was chromatographed on silica gel with a 20:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-4b0e2b50b64646d6b26ea3f7b2608932
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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