Dimethylformamide → HCID 54335965, compound

HRID 904027Notes

Reaction equation

HRID 904027 reaction equation
[Na+].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([NH:14][CH:15]3[C:22](=[O:23])[N:21]4[CH:16]3[S:17][CH2:18][C:19]([CH2:27][S:28][C:29]3[N:33]([CH3:34])[N:32]=[N:31][N:30]=3)=[C:20]4[C:24]([O-:26])=[O:25])=[O:13])=[CH:10][C:5]=2[CH2:4][CH2:3]1.ClCO[C:38](=[O:51])[C@H:39]([CH:48]([CH3:50])[CH3:49])[NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].[CH3:52]N(C)C=O>C(OCC)(=O)C>[C:44]([O:43][C:41]([NH:40][CH:39]([CH:48]([CH3:49])[CH3:50])[C:38]([CH2:52][O:25][C:24]([C:20]1[N:21]2[CH:16]([S:17][CH2:18][C:19]=1[CH2:27][S:28][C:29]1[N:33]([CH3:34])[N:32]=[N:31][N:30]=1)[CH:15]([NH:14][C:12](=[O:13])[CH2:11][C:9]1[CH:8]=[CH:7][C:6]3[O:2][CH2:3][CH2:4][C:5]=3[CH:10]=1)[C:22]2=[O:23])=[O:26])=[O:51])=[O:42])([CH3:45])([CH3:46])[CH3:47]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 54112037chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoateHCID 70590805HCID 70590805, compound

Product 1

HCID 54335965HCID 54335965, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 50 mmole of 7-[[(2,3-dihydro-5-benzofuranyl)acetyl]amino]-3-[[(1-methyltetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt and 50 mmole of N-tert-butoxycarbonyl-L-valine chloromethyl ester, prepared by the procedure described in W. German Offen. No. 2,236,620, are mixed in 100 ml of dimethylformamide and stirred for about 72 hours. The mixture is diluted with ethyl acetate, washed with water, with aqueous sodium bicarbonate, and with water a second time. The organic layer is dried over magnesium sulfate, filtered and evaporated to give 7-[[(2,3-dihydro-5-benzofuranyl)acetyl]amino]-3-[[(1-methyltetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-2-amino-3-methylbutyrylmethyl ester from which the amine protecting group is removed by standard procedures to give the title compound.

Workup

  1. customprepared by the procedure
  2. washwashed with water, with aqueous sodium bicarbonate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7652fa2bf5e94804b84fd1bbb4ac5773
Source dataset
uspto-grants-1980_10
Patent number
US04229575

Reaction notes

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