Methanol → (S)-N-Benzyl-N-methyl-2-[[(S)-2-[(1H-indol-3-yl)-1-carboxymethyl]-ethylamino]-N'-(t-butoxycarbonyl)-ethylamino]-3-phenyl-propionamide

HRID 235526Notes

Reaction equation

HRID 235526 reaction equation
[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26]C=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH2:41][C@H:42](N)[CH2:43]C(O)=O)=[CH:33]1.[C:48]([BH3-])#[N:49].[Na+].[CH3:52][OH:53].ClCCl.C[OH:58]>C(OCC)(=O)C>[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH2:48][NH:49][CH2:43][CH2:42][C@@H:41]([C:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[NH:32][CH:33]=1)[C:52]([OH:58])=[O:53])[C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 27615493-Amino-4-(1H-indol-3-yl)butanoic acid--hydrogen chloride (1/1)HCID 5003444Sodium cyanoborohydrideHCID 21226129Dichloromethane methanolHCID 53842533(S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Product 1

HCID 86750251(S)-N-Benzyl-N-methyl-2-[[(S)-2-[(1H-indol-3-yl)-1-carboxymethyl]-ethylamino]-N'-(t-butoxycarbonyl)-ethylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine (S)-N-benzyl-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (4.87 g, 11.87 mmol) and (S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((S)-tryptophan methyl ester hydrochloride salt) (3.02 g, 11.86 mmol) in methanol (120 mL). Add dropwise, a solution of sodium cyanoborohydride (9.5 mL, 1M in THF, 9.5 mmol) and stir under an inert atmosphere for 48 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 3% methanol/dichloromethane to give the title compound: TLC Rf =0.57 (silica gel, 10% methanol/dichloromethane).

Workup

  1. additionAdd dropwise
  2. concentrationConcentrate in vacuo
  3. customto obtain a residue
  4. extractionextract with water
  5. customSeparate the layers
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-ad513cc803714a2295328444a181eb0f
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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