Sodium cyanoborohydride → HCID 57081244, compound

HRID 1252519Notes

Reaction equation

HRID 1252519 reaction equation
O=[C:2]([CH3:28])[C@H:3]([NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH3:7])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:40][C@@H:41]([CH2:46][C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][CH:48]=1)[C:42]([O:44][CH3:45])=[O:43].C([BH3-])#N.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:45][O:44][C:42]([C@@H:41]([NH:40][C@H:2]([CH3:28])[C@H:3]([NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH3:7])=[O:5])[CH2:46][C:47]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][CH:48]=1)=[O:43]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 56625458HCID 56625458, compoundHCID 86742160HCID 86742160, compound

Product 1

HCID 57081244HCID 57081244, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of methyl (2S)-3-oxo-2-tritylaminobutyrate (2.00 g) and methyl (2S)-2-amino-3-(3-indolyl)propionate mono-p-toluenesulfonate (3.13 g) in methanol (30 ml) was added sodium cyanoborohydride (360 mg) and the mixture was stirred for 1 day at room temperature. The mixture was diluted with chloroform and washed successively with water and brine. The organic phase was separated and dried over magnesium sulfate, and the solvent was evaporated in vacuo. The residue was chromatographed on a silica gel (50 g) column and the elution was carried out with a mixture of n-hexane and ethyl acetate (4:1). The object fractions were collected and evaporated in vacuo to give methyl (2S,3R)-3-[[(1S)-1-methoxycarbonyl-2-(3-indolyl)ethyl]amino]-2-tritylaminobutyrate (625 mg) as a pale yellow oil.

Workup

  1. washwashed successively with water and brine
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was chromatographed on a silica gel (50 g) column
  6. washthe elution
  7. additionwas carried out with a mixture of n-hexane and ethyl acetate (4:1)
  8. customThe object fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-eed1bda0384c4b078736f5fd178965bf
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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