Triethylamine → Ammonia

HRID 1609180Notes

Reaction equation

HRID 1609180 reaction equation
[CH3:1][Si:2]([CH2:5][CH2:6][O:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C@@H:24]([CH2:27][C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)[CH2:25][OH:26])=[CH:18][CH:17]=1)=[O:9])([CH3:4])[CH3:3].C([N:35](CC)CC)C.[C:40](Cl)(=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44]>C(Cl)Cl.CO>[NH:31]1[CH:32]=[C:28]([CH2:27][CH:24]([N:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:8]([O:7][CH2:6][CH2:5][Si:2]([CH3:3])([CH3:4])[CH3:1])=[O:9])=[CH:17][CH:18]=2)[C:40](=[O:45])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:25][OH:26])[N:29]=[CH:30]1.[NH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 178504271HCID 178504271, compound

Product 2

HCID 222AmmoniaHCID 178447308HCID 178447308, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Reaction of 0.45 g of N-[(2'-(trimethylsilylethoxycarbonyl)biphenyl-4-yl)methyl]3-(imidazol-4-yl)-2-(S)-aminopropan-1-ol, 0.152 ml of triethylamine and 0.132 ml of valeryl chloride yields N-[3-(imidazol-4-yl)-1-hydroxy-2-propyl]-N-[(2'-(trimethylsilylethoxycarbonyl)biphenyl-4-yl)methyl]valeramide after flash chromatography (methylene chloride-methanol-conc. ammonia: 120-10-1). During working up, the aqueous phase is rendered slightly basic. FAB-MS: m/e=536 (M+H)+.

Sources & evidence

ORD record
ord-89d59d7dfb83403c94d8aea87008380e
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

Loading…