Citric Acid → HCID 53987300, compound

HRID 977528Notes

Reaction equation

HRID 977528 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, compoundYield 0.1%

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 cooled 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). The combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution to give the product (2.95 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (200 ml) was added to the residue
  3. extractionthe mixture was extracted with dichloromethane (50 ml×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=1/1 for elution

Sources & evidence

ORD record
ord-5fcf2839cc364d20baf6ca2c047b74d2
Source dataset
uspto-grants-1997_03
Patent number
US05614498

Reaction notes

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