Phosphoric Acid → [(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy)butanamide

HRID 1397814Notes

Reaction equation

HRID 1397814 reaction equation
P(=O)(O)(O)O.[C:6]([O:10][C:11]([NH:13][CH:14]([C:22](=[O:32])[NH:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:15]([OH:21])[C:16](OCC)=[O:17])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(C(C(C(OCC)=O)O)O)(OCC)=O.[BH4-].[Na+].[Na+].[Cl-]>O1CCCC1>[C:6]([O:10][C:11]([NH:13][CH:14]([CH:15]([OH:21])[CH2:16][OH:17])[C:22]([NH:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

7

Reactant 5

HCID 1004Phosphoric Acid2×HCID 5234Sodium ChlorideHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 4311764Sodium borohydrideHCID 86639530ethyl 3-[(tert-butoxy)carbonylamino]-2-hydroxy-3-[N-(phenylmethoxy) carbamoyl]propanoate

Product 1

HCID 86639529[(Tert-butoxy)carbonylamino]-3,4-dihydroxy-N-(phenylmethoxy)butanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To solution of tetrahydrofuran (THF, 6 L) and phosphoric acid buffer (0.025 M, KH2PO4/Na2HPO4; ratio 1/1, 2 L) containing ethyl 3-[(tert-butoxy)carbonylamino]-2-hydroxy-3-[N-(phenylmethoxy) carbamoyl]propanoate (compound prepared from diethyl tartrate according to the procedures described in Org. Synth., Coll. Vol. 1998, 220, J. Org. Chem. 1983, 3556 and U.S. Pat. No. 4,794,108) (120 g, 31.38 mmol), sodium borohydride (59.35 g, 156.9 mmol) was added portion wise at 0° C. over 1 h. The resulting mixture was stirred at 0° C. for an additional 1 h and at room temperature for 2 h. The micxture was cooled at 0° C. before addition of 1M aqueous solution containing H3PO4 until the pH reach 8. NaCl (100 g) was added to the mixture and the organic layer was separated. Extraction with ethyl acetate (3×1.5 L) was performed and the combined organic phases were washed with brine (1 L), dried over MgSO4 and evaporated under vacuo. The residue as purified by column chromatography using hexane/acetone as eluent to get 50 g of white solid.

Workup

  1. customthe organic layer was separated
  2. extractionExtraction with ethyl acetate (3×1.5 L)
  3. washthe combined organic phases were washed with brine (1 L)
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuo
  6. customThe residue as purified by column chromatography

Sources & evidence

ORD record
ord-a46118d69d5d4583b656f2e412e4db8f
Source dataset
uspto-grants-2014_12
Patent number
US08901293B2

Reaction notes

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