Citric Acid → HCID 53907908, compound

HRID 849868Notes

Reaction equation

HRID 849868 reaction equation
C(O[C:4](=[O:25])[CH2:5][O:6][CH2:7][C@H:8]([NH:16][CH2:17]C(OC(C)(C)C)=O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.[Li].[CH2:27]([OH:29])C.C(O)(=O)[CH2:31][C:32]([CH2:37]C(O)=O)([C:34](O)=O)[OH:33]>C1COCC1>[C:32]([O:33][C:27](=[O:29])[N:16]([C@@H:8]([CH2:7][O:6][CH2:5][CH2:4][OH:25])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:17])([CH3:31])([CH3:34])[CH3:37]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 3028194LithiumHCID 54367719HCID 54367719, compound

Product 1

HCID 53907908HCID 53907908, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

((2R)-2-(tert-Butoxycarbonylmethylamino)-3-phenylpropoxy)acetic acid ethyl ester (0.50 g, 1.42 mmol) was dissolved in THF (4 mL). Lithium boronhydride (1.56 mL of a 2.0 M solution in THF, 3.13 mmol) was added dropwise. Ethanol (8 mL) was added. The reaction mixture was stirred 16 h at room temp. The solution was acidified with 10% citric acid to pH=4. The solvent was removed in vacuo. The residue was dissolved in water (50 mL). This solution was extracted with dichloromethane (3×40 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (30 g) with dichloromethane/ethyl acetate 1:1 as eluent to give 0.29 g of N-((1R)-1-(2-hydroxyethoxymethyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionThis solution was extracted with dichloromethane (3×40 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (30 g) with dichloromethane/ethyl acetate 1:1 as eluent

Sources & evidence

ORD record
ord-d660cd007d6f405f9f9b6fbd6cc31ba7
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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