Methanol → HCID 67930949, compound

HRID 2294709Notes

Reaction equation

HRID 2294709 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:16][C:17](=[O:64])[C@@H:18]([NH:44]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:19][C:20]2[N:21]=[CH:22][N:23]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=2)[C@@H:9]([OH:15])[C@H:10]([CH:12]2[CH2:14][CH2:13]2)[OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.FC(F)(F)C(O)=O.C(=O)(O)[O-].[K+]>C(Cl)Cl>[NH2:44][C@@H:18]([CH2:19][C:20]1[N:21]=[CH:22][N:23]([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=1)[C:17]([NH:16][C@@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C@@H:9]([OH:15])[C@H:10]([CH:12]1[CH2:13][CH2:14]1)[OH:11])=[O:64]

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 516893Potassium BicarbonateHCID 86751645HCID 86751645, compound

Product 1

HCID 67930949HCID 67930949, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.52 g (1.79 mmol) of (S)-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-trityl-α-(tritylamino)imidazole-4-propionamide in a mixture of 95.5 ml of methylene chloride, 3 ml of methanol and 1.5 ml of trifluoroacetic acid is stirred at room temperature for 5 minutes. Subsequently, 150 ml of 2N potassium bicarbonate solution and 150 ml of methylene chloride are added. The organic phase is separated, dried over sodium sulphate and evaporated. For purification, the residue is chromatographed on 100 g of silica gel using a 150:10:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 1.03 g of (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-tritylimidazole-4-propionamide as a colourless foam; MS: 607 (M+H)+.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customFor purification
  5. customthe residue is chromatographed on 100 g of silica gel using
  6. additiona 150:10:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-fb43f96dc31948deb07f320b5f71fe71
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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