Triethylamine → HCID 22879400, compound

HRID 2294721Notes

Reaction equation

HRID 2294721 reaction equation
[NH2:1][CH:2]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH:3]([OH:9])[CH:4]([CH:6]1[CH2:8][CH2:7]1)[F:5].[C:17]([O:21][C:22]([N:24]1[CH:28]=[C:27]([CH2:29][C@H:30]([NH:34][C:35](=[O:52])[C@@H:36]([CH2:44][S:45]([C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:47])=[O:46])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:31](O)=[O:32])[N:26]=[CH:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.C1C=C2C(N(O)N=NC2=CC=1)=O>CN(C)C=O>[C:48]([S:45]([CH2:44][C@@H:36]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:35]([NH:34][C@@H:30]([CH2:29][C:27]1[N:26]=[CH:25][N:24]([C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:23])[CH:28]=1)[C:31]([NH:1][C@@H:2]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@@H:3]([OH:9])[C@H:4]([CH:6]1[CH2:8][CH2:7]1)[F:5])=[O:32])=[O:52])(=[O:47])=[O:46])([CH3:49])([CH3:50])[CH3:51]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 21692242HCID 21692242, compoundHCID 22862631HCID 22862631, compound

Product 1

HCID 22879400HCID 22879400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 147 mg (0.64 mmol) of (1S or R,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1-fluoro-2-butanol, 365 mg (0.7 mmol) of (S)-1-(tert-butoxycarbonyl)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionic acid, 71 mg (0.7 mmol) of triethylamine, 114 mg (0.7 mmol) of HOOBT and 285 mg (0.7 mmol) of HOBTU in 15 ml of dimethylformamide is stirred at room temperature overnight under argon. Thereafter, the dimethylformamide is evaporated in a high vacuum and the residue is taken up in 50 ml of ethyl acetate. The ethyl acetate phase is washed with 20 ml of saturated sodium bicarbonate solution and 20 ml of saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. There is obtained (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-3-fluoro-2-hydroxypropyl]-1-Boc-imidazole-4-propionamide as a yellowish foam.

Workup

  1. customThereafter, the dimethylformamide is evaporated in a high vacuum
  2. washThe ethyl acetate phase is washed with 20 ml of saturated sodium bicarbonate solution and 20 ml of saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e49c0e4bb4b8464e932602a83fc5809e
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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