Dimethylformamide → HCID 70592145, compound

HRID 904026Notes

Reaction equation

HRID 904026 reaction equation
CN(C)[CH:3]=[O:4].[Na].[C:7]([O:10][CH2:11][C:12]1[CH2:19][S:18][CH:17]2[N:14]([C:15](=[O:41])[CH:16]2[NH:20][C:21](=[O:40])[C:22]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([NH2:32])[C:23]2[CH:24]=[CH:25][C:26]3[O:30][CH2:29][CH2:28][C:27]=3[CH:31]=2)[C:13]=1[C:42]([OH:44])=[O:43])(=[O:9])[CH3:8].ClC[CH2:47][C:48]([CH3:53])([CH3:52])[C:49]([O-])=[O:50]>C(OCC)(=O)C>[C:49]([O:4][CH2:3][O:43][C:42]([C:13]1[N:14]2[CH:17]([S:18][CH2:19][C:12]=1[CH2:11][O:10][C:7](=[O:9])[CH3:8])[CH:16]([NH:20][C:21](=[O:40])[C:22]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])([NH2:32])[C:23]1[CH:24]=[CH:25][C:26]3[O:30][CH2:29][CH2:28][C:27]=3[CH:31]=1)[C:15]2=[O:41])=[O:44])(=[O:50])[C:48]([CH3:53])([CH3:52])[CH3:47]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 5360545SodiumHCID 217530474-Chloro-2,2-dimethylbutanoateHCID 70590452HCID 70590452, compound

Product 1

HCID 70592145HCID 70592145, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To dimethylformamide is added the sodium salt of 3-[(acetyloxy)methyl]-7-[[(tert-butoxycarbonyl)amino(2,3-dihydro-5-benzofuranyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid one equivalent, and the solution is stirred at room temperature for about 30 minutes after which an equivalent of chloromethylpivalate is added. Stirring is continued for about 3 hours. The solution is diluted with ethyl acetate and washed with water. The organic layer is separated and evaporated to dryness. The residue is recrystallized from ethyl acetate to give the title compound.

Workup

  1. additionis added
  2. washwashed with water
  3. customThe organic layer is separated
  4. customevaporated to dryness
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1f9987e21401474a88b1010abf93973e
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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