Sodium Hydroxide → HCID 2733678, compound

HRID 1171454Notes

Reaction equation

HRID 1171454 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-2023e42d71914f8291dbf2b989ede45b
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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