Methanol → HCID 15222817, compound

HRID 2256433Notes

Reaction equation

HRID 2256433 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=1)[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].CO>O1CCCC1>[CH2:11]([O:10][C:8]([NH:7][C@@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=1)[CH2:5][OH:4])=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 54105556HCID 54105556, compound

Product 1

HCID 15222817HCID 15222817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

31.80 g (848.4 mmol) of sodium borohydride is added to a solution of 221.41 g (605.9 mmol) of (S)-N-benzyloxycarbonyl-O-ethyltyrosine methyl ester in 1.5 l of tetrahydrofuran at room temperature. 270 ml of methanol is instilled in it with stirring within 2 hours. Then, the tetrahydrofuran is distilled off in a vacuum, the residue is taken up in 1 l of water and extracted three times with 700 ml of ethyl acetate. The combined organic phase is washed with water, dried with sodium sulfate and concentrated. It is recrystallized from ethyl acetate/hexane.

Workup

  1. distillationThen, the tetrahydrofuran is distilled off in a vacuum
  2. extractionextracted three times with 700 ml of ethyl acetate
  3. washThe combined organic phase is washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customIt is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ca676b21fccb409db2048e3540a915dd
Source dataset
uspto-grants-1997_08
Patent number
US05654467

Reaction notes

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