Hydrochloric Acid → HCID 58458990, compound

HRID 969778Notes

Reaction equation

HRID 969778 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:16]1[CH2:18][CH2:17]1)[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@@H:12]([CH:16]1[CH2:18][CH2:17]1)[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67033893(S)-Benzyloxycarbonylamino-cyclopropyl-acetic acid

Product 1

HCID 58458990HCID 58458990, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (S)-benzyloxycarbonylamino-cyclopropyl-acetic acid (3.2 g, 12.8 mmol) in THF (20 mL) was cooled in an ice/water bath and treated with a 1 M solution of BH3 in THF (16.7 mL, 16.7 mmol). The reaction was stirred for 4 hours and then treated with 1 M HCl until the bubbling ceased. The reaction was stirred overnight and the organic solvent was removed by rotary evaporation. The residue was treated with ethyl acetate and transferred to a separatory funnel. The aqueous phase was discarded and the organics were washed twice with 1 M NaOH, dried over MgSO4 and the solvent was removed. The residue was purified on silica gel using a gradient of 0-100% ethyl acetate in hexane to afford 1.5 g (50% yield) of (S)-(1-Cyclopropyl-2-hydroxy-ethyl)-carbamic acid benzyl ester as a white solid; 1H NMR (CDCl3, 400 MHz) δ 0.26-0.37 (m, 1H), 0.34-0.44 (m, 1H), 0.47-0.61 (m, 2H), 0.83-0.94 (m, 1H), 2.95-3.04 (m, 1H), 3.70 (dd, 1H, J1=5.8, J2=11.1), 3.79-3.88 (m, 1H), 5.00-5.12 (m, 1H), 5.10 (s, 2H), 7.29-7.31 (m, 5H); HPLC-MS calcd. for C13H17NO3(M+H+) 236.1, found 236.3.

Workup

  1. stirringThe reaction was stirred overnight
  2. customthe organic solvent was removed by rotary evaporation
  3. additionThe residue was treated with ethyl acetate
  4. customtransferred to a separatory funnel
  5. washthe organics were washed twice with 1 M NaOH
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed
  8. customThe residue was purified on silica gel using a gradient of 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d97cff38ef234f50b816850cac942e1c
Source dataset
uspto-grants-2007_12
Patent number
US07307095B2

Reaction notes

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