HCID 86737774, compound → HCID 70548116, compound

HRID 894384Notes

Reaction equation

HRID 894384 reaction equation
[CH3:1][C:2]1([CH3:27])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:26])[C@H:10]([CH:11]([OH:25])[C:12]3[CH:17]=[CH:16][C:15]([O:18]C4CCCCO4)=[CH:14][CH:13]=3)[C@H:4]2[S:3]1>CC(C)=O.P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:27])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:26])[C@H:10]([CH:11]([OH:25])[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C@H:4]2[S:3]1

Participants

5

Reactant 1

HCID 86737774HCID 86737774, compound

Product 1

HCID 70548116HCID 70548116, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1004Phosphoric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethyl-3α-cyano-6α-[p-(2-tetrahydropyranyloxy)-α-hydroxybenzyl]penam (45 mg, 0.12 mmol) is dissolved in 3 ml of acetone and 0.5 ml of 10% phosphoric acid. After stirring 18 hours at room temperature, the solution is diluted with a 10 fold excess of ethyl acetate and washed with saturated sodium chloride. Purification of the crude phenol (42 mg) by PLC (35% acetone/toluene) provides 2,2-dimethyl-3α-cyano-6α-(p-hydroxy-α-hydroxybenzyl)penam.

Workup

  1. washwashed with saturated sodium chloride
  2. customPurification of the crude phenol (42 mg) by PLC (35% acetone/toluene)

Sources & evidence

ORD record
ord-acae7a645fc64e3d86cea4b8e49bbc70
Source dataset
uspto-grants-1981_08
Patent number
US04283531

Reaction notes

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