Hydrochloric Acid → HCID 59712339, compound

HRID 2222438Notes

Reaction equation

HRID 2222438 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:13]([C:15]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][CH2:16]1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.Cl>C(O)C.O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:13]([OH:14])[C:15]2([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 59712531HCID 59712531, compound

Product 1

HCID 59712339HCID 59712339, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.974 g of methyl 1-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxybenzoyl)-1-cyclopropanecarboxylate in 30 ml of ethanol and 10 ml of tetrahydrofuran was added 0.112 g of sodium borohydride, and the mixture was stirred at room temperature for 15 hours. 50 ml of water, 100 ml of ethyl acetate and 5 ml of hydrochloric acid (2N) were added, and the organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 0.483 g of the title compound as a colorless oil.

Workup

  1. dry with materialthe organic layer was dried over magnesium sulfate
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-917fce26ac3449cc99387e2078d8b124
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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