Triethylamine → HCID 22879358, compound

HRID 2294703Notes

Reaction equation

HRID 2294703 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].Br[CH2:46][C:47](=[CH2:53])[C:48]([O:50][CH2:51][CH3:52])=[O:49].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:10]([NH:12][C@H:13]([C:14](=[O:15])[NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:22][CH2:23]1)[OH:20])[CH2:32][C:33]1[N:34]=[CH:35][N:36]([CH2:53][C:47](=[CH2:46])[C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH:37]=1)=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 178455612HCID 178455612, compound

Product 1

HCID 22879358HCID 22879358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 100 mg (0.16 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide, 46 mg (0.24 mmol) of ethyl 2-(bromomethyl)acrylate and 0.044 ml (0.32 mmol) of triethylamine in 3 ml of methylene chloride is stirred at room temperature under argon for 24 hours. Subsequently, the reaction mixture is evaporated and, for purification, the residue is chromatographed on 30 g of silica gel using a 14:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained mg of ethyl 4-[(S)-2-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-2-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]ethyl]-α-methyleneimidazole-1-propionate as an amorphous solid; MS: 743 (M+H)+.

Workup

  1. customSubsequently, the reaction mixture is evaporated and, for purification
  2. customthe residue is chromatographed on 30 g of silica gel using
  3. additiona 14:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-e995d275defd431ab194c3bb1d27259c
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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