Citric Acid → HCID 53987300, compound

HRID 1440170Notes

Reaction equation

HRID 1440170 reaction equation
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([C:7](OC)=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(O)C>[C:14]([O:13][C:11]([NH:1][C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:7][OH:8])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 75487913(R)-Methyl 2-((tert-butoxycarbonyl)amino)hexanoate

Product 1

HCID 53987300HCID 53987300, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-DNle-OMe (4.23 g) in dry THF (30 ml) were added lithium chloride (0.85 g), sodium borohydride (0.76 g) and dry ethanol (60 ml), and the mixture was stirred at the same temperature for 2 h and at room temperature over night. The mixture was with ice-water, adjusted to pH 3 by the gradual addition of 10% aq. citric acid, and concentrated in vacuo. Water (200 ml) was added to the residue,and the mixture was extracted with dichloromethane (50 ml×3).

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (200 ml) was added to the residue,and the mixture
  3. extractionwas extracted with dichloromethane (50 ml×3)

Sources & evidence

ORD record
ord-5fbfdaf4f8f5417a838cd3fce1b8ee91
Source dataset
uspto-grants-1996_03
Patent number
US05496928

Reaction notes

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