Ammonium Chloride → HCID 178456007, compound

HRID 1655743Notes

Reaction equation

HRID 1655743 reaction equation
[CH2:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][C:11](=[O:13])[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C@@H:18]([CH2:39][C:40]1[N:41]=[CH:42][NH:43][CH:44]=1)[C:19]([NH:21][C@@H:22]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C@@H:23]([OH:31])[CH2:24][C@@H:25]([CH:28]([CH3:30])[CH3:29])[CH:26]=[CH2:27])=[O:20].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl-].[NH4+]>CN(C)C=O.C(#N)C>[CH2:1]([NH:8][C@H:9]([CH2:10][C:11](=[O:13])[NH2:12])[C:14]([NH:17][C@@H:18]([CH2:39][C:40]1[N:41]=[CH:42][NH:43][CH:44]=1)[C:19]([NH:21][C@@H:22]([CH2:32][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)[C@@H:23]([OH:31])[CH2:24][C@@H:25]([CH:28]([CH3:29])[CH3:30])[CH:26]=[CH2:27])=[O:20])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 53942189HCID 53942189, compoundHCID 178456019HCID 178456019, compound

Product 1

HCID 178456007HCID 178456007, compoundYield 32.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 100 mg (0.45 mmol) of N-benzyl-3-carbamoyl-D-alanine, 187 mg (0.45 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy 4-isopropyl-5-hexenyl]imidazole-4-propionamide 0.093 ml of Hunig base and 202 mg of BOP in 10 ml of a 2:1 mixture of acetonitrile and dimethylformamide was stirred at room temperature for 18 hours. Thereafter, the reaction mixture was poured into aqueous ammonium chloride solution, extracted with ethyl acetate, the extracts were washed with sodium carbonate solution, dried over sodium sulfate and evaporated to dryness under reduced pressure. Chromatography of the residue on silica gel with 10% methanol in methylene chloride as the eluting agent yielded 87 mg (32%) of (S)-α-[(R)-2-(benzylamino) 3-carbamoylpropionamido]-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide as a resin. MS: 595 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extracts were washed with sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-40f7ffe93fe347d7a0f7c3c5fa0f2d8e
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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