Hydrochloric Acid → HCID 86747372, compound

HRID 257440Notes

Reaction equation

HRID 257440 reaction equation
CC(C)(OC([NH:7][C@@H:8]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:11]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:10]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:9]1[CH:37]([OH:44])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=O)C.Cl>C(OCC)C>[NH2:7][C@@H:8]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@@H:11]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:10]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:9]1[CH:37]([OH:44])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86747370HCID 86747370, compound

Product 1

HCID 86747372HCID 86747372, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve [1R,2S,3R,4S,5R]-2-[[(1,1-dimethylethoxy)carbonyl]amino]-β-hydroxy-3,4,5-tris(phenylmethoxy)cyclopentanepropanoic acid, ethyl ester (160 mg, 0.258 mmol) in ethyl ether (20 mL) and cool to 0°-5° C. with an ice bath. Bubble hydrogen chloride gas into the solution for 25-30 minutes. Remove the ice bath and evaporate the ethyl ether to 1/2 volume with a stream of nitrogen. Add fresh ethyl ether and carefully add aqueous sodium hydrogen carbonate. Separate the organic phase and extract the aqeuous phase with ethyl acetate. Combine the organic phases, wash with aqueous sodium chloride, dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as a mixture of epimers (140 mg).

Workup

  1. temperaturecool to 0°-5° C. with an ice bath
  2. customRemove the ice bath
  3. customevaporate the ethyl ether to 1/2 volume with a stream of nitrogen
  4. additionAdd fresh ethyl ether and carefully add aqueous sodium hydrogen carbonate
  5. customSeparate the organic phase
  6. extractionextract the aqeuous phase with ethyl acetate
  7. washwash with aqueous sodium chloride
  8. dry with materialdry (MgSO4)
  9. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-d63152a58faa472a823ff541dcb56b43
Source dataset
uspto-grants-1993_11
Patent number
US05262425

Reaction notes

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