chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoate → 7-[[2-carbethoxy-2-(1H-indol-1-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-2-amino-3-methylbutyryloxymethyl ester

HRID 904013Notes

Reaction equation

HRID 904013 reaction equation
[Na+].[C:2]([CH:7]([N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32]1)[C:8]([NH:10][CH:11]1[C:18](=[O:19])[N:17]2[CH:12]1[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]1[S:26][C:27]([CH3:30])=[N:28][N:29]=1)=[C:16]2[C:20]([O-:22])=[O:21])=[O:9])([O:4][CH2:5][CH3:6])=[O:3].Cl[CH2:41][O:42][C:43](=[O:56])[C@H:44]([CH:53]([CH3:55])[CH3:54])[NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47]>CN(C)C=O.C(OCC)(=O)C>[C:49]([O:48][C:46]([NH:45][CH:44]([CH:53]([CH3:55])[CH3:54])[C:43]([O:42][CH2:41][O:21][C:20]([C:16]1[N:17]2[CH:12]([S:13][CH2:14][C:15]=1[CH2:23][S:24][C:25]1[S:26][C:27]([CH3:30])=[N:28][N:29]=1)[CH:11]([NH:10][C:8](=[O:9])[CH:7]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:31]1[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32]1)[C:18]2=[O:19])=[O:22])=[O:56])=[O:47])([CH3:52])([CH3:51])[CH3:50]

Participants

5

Reactant 2

HCID 54112037chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoateHCID 705826667-[[2-carbethoxy-2-(1H-indol-1-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

Product 1

HCID 543106627-[[2-carbethoxy-2-(1H-indol-1-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-2-amino-3-methylbutyryloxymethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5 grams of 7-[[2-carbethoxy-2-(1H-indol-1-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]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, prepared by the general procedure described in W. German Offen. No. 2,236,620 are mixed in 100 ml of dimethylformamide (DMF) and stirred for 72 hours. The mixture is diluted with ethyl acetate, washed with water, aqueous sodium bicarbonate and again with water. The ethyl acetate portion is dried over magnesium sulfate, filtered and evaporated to dryness to give 7-[[2-carbethoxy-2-(1H-indol-1-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]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. customprepared by the general procedure
  2. washwashed with water, aqueous sodium bicarbonate and again with water
  3. dry with materialThe ethyl acetate portion is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e51c995eeb6e48a6b89ab9255b947561
Source dataset
uspto-grants-1980_10
Patent number
US04229574

Reaction notes

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