Hydrochloric Acid → HCID 11734568, compound

HRID 1584356Notes

Reaction equation

HRID 1584356 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:30])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C@@H:22]([OH:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:15][C:14]=2[O:28][CH3:29])[N:10]=1.Cl[C:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:33].O.Cl>N1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:30])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C@@H:22]([O:27][C:32]([O:34][C:35]3[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=3)=[O:33])[C:23]([O:25][CH3:26])=[O:24])=[CH:15][C:14]=2[O:28][CH3:29])[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 821294-Nitrophenyl chloroformateHCID 11101768HCID 11101768, compound

Product 1

HCID 11734568HCID 11734568, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl (R)-(-)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxy-pentanoate (3.15 g) in pyridine (50 ml) was added 4-nitrophenyl chloroformate (2.3 g), in limited amounts, at room temperature. The mixture was stirred for one hour. The reaction mixture was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:2), was obtained methyl (R)-(+)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-(4-nitrophenoxycarbonyloxy)pentanoate (4.3 g, 98%).

Workup

  1. customat room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-6ddd8dfa5b66499f8dabf4f8323b9a58
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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