Sodium Hydroxide → HCID 2733678, compound

HRID 351391Notes

Reaction equation

HRID 351391 reaction equation
C[O:2][C:3]([C@H:5]1[C@@H:10]([NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:9][CH:8]=[CH:7][CH2:6]1)=[O:4].[OH-].[Na+]>CO.O>[CH2:15]([O:14][C:12]([NH:11][C@@H:10]1[C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH:7]=[CH:8][CH2:9]1)=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14320501HCID 14320501, compound

Product 1

HCID 2733678HCID 2733678, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A sample of (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid methyl ester (91.4 g) was dissolved in MeOH (500 mL) prior to the dropwise addition of NaOH (25.3 g) in water (95 mL). After 3 h, the solution was partially concentrated and an Et2O/water mixture was added. The aqueous layer was separated and was acidified (pH ˜2) with concentrated HCl. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with water and brine before they were dried, filtered, and concentrated to give (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (72.7 g). MS found: (M+H)+=276.2.

Workup

  1. concentrationthe solution was partially concentrated
  2. additionan Et2O/water mixture was added
  3. customThe aqueous layer was separated
  4. extractionThe resulting mixture was extracted with EtOAc
  5. washThe combined organic layers were washed with water and brine before they
  6. customwere dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f1adf113e2a840bf95f34ad684f43092
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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