Sodium → HCID 86737359, compound

HRID 225322Notes

Reaction equation

HRID 225322 reaction equation
[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH2:28][O:29][CH3:30])[CH:22]=1)[C:3]([NH:5][C:6]1([O:19][CH3:20])[C:13](=[O:14])[N:12]2[CH:7]1[S:8][CH2:9][C:10]([CH3:18])=[C:11]2[C:15]([OH:17])=[O:16])=[O:4].[Na].Cl[CH2:33][O:34][C:35](=[O:48])[C@H:36]([CH:45]([CH3:47])[CH3:46])[NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][CH:2]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH2:28][O:29][CH3:30])[CH:22]=1)[C:3]([NH:5][C:6]1([O:19][CH3:20])[C:13](=[O:14])[N:12]2[CH:7]1[S:8][CH2:9][C:10]([CH3:18])=[C:11]2[C:15]([O:17][CH2:33][O:34][C:35](=[O:48])[CH:36]([NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[CH:45]([CH3:47])[CH3:46])=[O:16])=[O:4]

Participants

6

Reactant 3

HCID 5360545SodiumHCID 23329780HCID 23329780, compoundHCID 54112037chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoate

Product 1

HCID 86737359HCID 86737359, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5 grams of 7-[[amino[4-hydroxy-3-(methoxymethyl)phenyl]acetyl]amino]-7-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, sodium salt and 8.5 grams of N-tert-butoxycarbonyl-L-valine chloromethyl ester, which is prepared by the general procedure described in W. German Offen. No. 2,236,620, are mixed in 100 ml of dimethylformamide and stirred for 72 hours. The mixture is diluted with ethyl acetate, washed with water and aqueous bicarbonate and again with water. The ethyl acetate portion is dried over magnesium sulfate, filtered and evaporated to give 7-[[amino[4-hydroxy-3-(methoxymethyl)phenyl]acetyl]amino]-7-methoxy-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, N-tert-butoxycarbonyl-2-amino-3-methylbutyryloxymethyl ester from which the protecting group can be removed by standard procedures to give the title compound.

Workup

  1. customis prepared by the general procedure
  2. washwashed with water and aqueous bicarbonate and again with water
  3. dry with materialThe ethyl acetate portion is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-badfa37ca2f44bcc90097ae8af996e05
Source dataset
uspto-grants-1980_11
Patent number
US04236002

Reaction notes

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