Sodium Chloride → HCID 86747370, compound

HRID 257439Notes

Reaction equation

HRID 257439 reaction equation
[CH3:1][C:2]([CH3:54])([O:4][C:5]([N:7](CC1C=CC(OC)=CC=1)[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:6])[CH3:3].C(#N)C.O.[Cl-].[Na+]>O.C(OCC)(=O)C>[CH3:54][C:2]([CH3:3])([O:4][C:5]([NH: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:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:10]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@H:9]1[CH:37]([OH:44])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 18373917Acetonitrile--water (1/1)HCID 86747371HCID 86747371, compound

Product 1

HCID 86747370HCID 86747370, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve [1R,2S,3R,4S,5R]-2-[[(1,1-dimethylethoxy)carbonyl][(4-methoxyphenyl)methyl]amino]-β-hydroxy-3,4,5-tris(phenylmethoxy)-cyclopentanepropanoic acid, ethyl ester (2.018 g, 2.73 mmol) in a 4:1 mixture of acetonitrile/water (75 mL) and cool to 0° C. with an ice bath. Add ceric ammonium nitrate (4.23 g, 7.72 mmol) and stir for 1 hour. Pour into a mixture of water/ethyl acetate containing sodium chloride, separate the organic phase, wash with dilute sodium hydrogen carbonate and aqueous sodium chloride. Dry (MgSO4), evaporate the solvent in vacuo and subject to Kugelrohr distillation to remove p-methoxybenzaldehyde (94° C. @ high vacuum) to give the title compound remaining as a white solid which is recrystallized from cyclohexane.

Workup

  1. customseparate the organic phase
  2. washwash with dilute sodium hydrogen carbonate and aqueous sodium chloride
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. distillationsubject to Kugelrohr distillation
  6. customto remove p-methoxybenzaldehyde (94° C. @ high vacuum)

Sources & evidence

ORD record
ord-edc176874c294ef9ab25590c1f6a4a31
Source dataset
uspto-grants-1993_11
Patent number
US05262425

Reaction notes

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