Sodium borohydride → HCID 54348451, compound

HRID 2398849Notes

Reaction equation

HRID 2398849 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][O:9][C:10]([NH:12][C@H:13]([C:22](OC)=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[O:11])=[CH:6][CH:5]=1>CO>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([NH:12][C@H:13]([CH2:22][OH:23])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[O:11])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53845586HCID 53845586, compound

Product 1

HCID 54348451HCID 54348451, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 150 ml of 50% aqueous methanol, 13.1 g of sodium borohydride was added with stirring while cooling with ice. To the mixture was added dropwise 250 ml of a methanol solution containing 26.5 g of methyl N-(4-methylbenzyloxycarbonyl)-tyrosinate. The mixture was stirred while cooling with ice for two hours and at room temperature for four hours. After neutralization with 10% hydrochloric acid, the mixture was concentrated in vacuo and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum ether to give 17.9 g of N-(4-methylbenzyloxycarbonyl)-tyrosinol: yield 74%; mp. 128°-129° C. Analysis, calculated for C18H21O4N: C, 68.55; H, 6.72; N, 4.44; found C, 68.51; H, 6.84; N, 4.29.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture was stirred
  3. concentrationAfter neutralization with 10% hydrochloric acid, the mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-3cb1e07321f444a59566b1b72fddd087
Source dataset
uspto-grants-1977_05
Patent number
US04025644

Reaction notes

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