Tetrahydrofuran → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614137Notes

Reaction equation

HRID 614137 reaction equation
O1CCCC1.[C:6]1([C:12]([NH:25][CH:26]2[C:44](=[O:45])[N:28]3[CH:29]([C:34]4[N:38](C(OCC)=O)[N:37]=[N:36][N:35]=4)[C:30]([CH3:33])([CH3:32])[S:31][C@H:27]23)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[C:6]1([C:12]([NH:25][CH:26]2[C:44](=[O:45])[N:28]3[CH:29]([C:34]4[NH:35][N:36]=[N:37][N:38]=4)[C:30]([CH3:32])([CH3:33])[S:31][C@H:27]23)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 867342306-(Triphenylmethylamino)-2,2-dimethyl-3-(1-[ethoxycarbonyl]tetrazol-5-yl)penam

Product 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 2 ml. of tetrahydrofuran and 4 ml. of water is added 150 mg. of 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[ethoxycarbonyl]tetrazol-5-yl)penam. The pH of the mixture is adjusted to 9.5, and stirring is continued at that pH for a further 30 minutes, at ambient temperature. The bulk of the tetrahydrofuran is removed by evaporation in vacuo, and the residue is portioned between water and ethyl acetate at pH 9. The ethyl acetate is removed and discarded. Fresh ethyl acetate is added and the pH is adjusted to 2.0. The ethyl acetate layer is removed, washed with water, dried using anhydrous sodium sulfate, and evaporated in vacuo to give the crude title compound.

Workup

  1. additionTo a stirred mixture of 2 ml
  2. customThe bulk of the tetrahydrofuran is removed by evaporation in vacuo
  3. customThe ethyl acetate is removed
  4. additionFresh ethyl acetate is added
  5. customThe ethyl acetate layer is removed
  6. washwashed with water
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-ef4d77f0722b4b0b8c1a3a2bbfb9e529
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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