Triethylamine → HCID 86734117, compound

HRID 1729674Notes

Reaction equation

HRID 1729674 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[NH2:34][C@@H:35]1[C:47](=[O:48])[N:37]2[C@@H:38]([C:44]([OH:46])=[O:45])[C@@:39]([Cl:43])([CH3:42])[CH2:40][S:41][C@H:36]12>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([NH:34][C@@H:35]1[C:47](=[O:48])[N:37]2[C@@H:38]([C:44]([OH:46])=[O:45])[C@@:39]([Cl:43])([CH3:42])[CH2:40][S:41][C@H:36]12)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 68139899HCID 68139899, compound

Product 1

HCID 86734117HCID 86734117, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of α-tert.-butoxycarbonylaminophenylacetic acid (1.0 g) and triethylamine (405 mg) in tetrahydrofuran (16 ml), is added isobutylchloroformate (550 mg) at -10°C and the mixture is stirred for 10 minutes. To the solution is added a solution of 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylic acid (870 mg), and triethylamine (405 mg) in a mixture of tetrahydrofuran and water (1:1; 15 ml), and the mixture is stirred for 1 hour at 5°C, and for 1 hour at room temperature. The reaction mixture is evaporated in vacuo to remove tetrahydrofuran, and the resultant solution is diluted with a mixture of water and ethyl acetate (3:1). The aqueous layer is separated, acidified to pH 3 with 10% hydrochloric acid, and extracted with ethyl acetate. The extract solution is washed with water, dried, and evaporated to give 7β-(α-tert.-butoxycarbonylaminophenylacetamido)-3β-chloro-3α-methylcepham-4α-carboxylic acid (1.5 g). Yield: 77%.

Workup

  1. stirringthe mixture is stirred for 1 hour at 5°C
  2. waitfor 1 hour at room temperature
  3. customThe reaction mixture is evaporated in vacuo
  4. customto remove tetrahydrofuran
  5. additionthe resultant solution is diluted with a mixture of water and ethyl acetate (3:1)
  6. customThe aqueous layer is separated
  7. extractionextracted with ethyl acetate
  8. washThe extract solution is washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-5d1a5eaf999d407ea46254146c314f50
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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