Diethyl Ether → 2-(2-Amino-1,3-thiazol-4-yl)-2-{1-[3-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxyimino}acetic acid tert-butyl ester.hydrochloride

HRID 1383127Notes

Reaction equation

HRID 1383127 reaction equation
[C:1]([O:5][C:6](=[O:23])[C:7]([C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)=[N:8][O:9][C:10]([C:13](=[O:16])[NH:14][NH2:15])([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:36]([O:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[O:49][C:50](=[O:52])[CH3:51])[C:43]([Cl:45])=[O:44])(=[O:38])[CH3:37].CCOCC>C(Cl)Cl.CO>[ClH:45].[C:1]([O:5][C:6](=[O:23])[C:7]([C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)=[N:8][O:9][C:10]([C:13](=[O:16])[NH:14][NH:15][C:43](=[O:44])[C:42]1[CH:46]=[CH:47][C:48]([O:49][C:50](=[O:52])[CH3:51])=[C:40]([O:39][C:36](=[O:38])[CH3:37])[CH:41]=1)([CH3:12])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 140969484-(Chlorocarbonyl)-1,2-phenylene diacetateHCID 545002132-(2-Amino-1,3-thiazol-4-yl)-2-(1-carbazoyl-1-methylethoxyimino)acetic acid tert-butyl ester

Product 1

HCID 884942922-(2-Amino-1,3-thiazol-4-yl)-2-{1-[3-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxyimino}acetic acid tert-butyl ester.hydrochlorideYield 97.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride was suspended 0.7 g (1.74 mmole) of 2-(2-amino-1,3-thiazol-4-yl)-2-(1-carbazoyl-1-methylethoxyimino)acetic acid tert-butyl ester, and to the suspension was added 2.16 g (10.6 mmole) of N,O-bis(trimethylsilyl)acetamide to form a solution. To the ice-cooled solution was added 0.488 g (1.9 mmole) of 3,4-diacetoxybenzoic acid chloride and the mixture was stirred for one hour under ice-cooling. The resulting mixture was poured into 150 ml of ether and to the mixture was added a small amount of methanol while stirring. Resulting precipitates were collected by filtration, washed with ether and then dried to obtain 0.96 g of 2-(2-amino-1,3-thiazol-4-yl)-2-{1-[3-(3,4-diacetoxybenzoyl)carbazoyl]-1-methylethoxyimino}acetic acid tert-butyl ester.hydrochloride. (Yield: 97.9%)

Workup

  1. customto form a solution
  2. temperaturecooling
  3. stirringwhile stirring
  4. customResulting
  5. customprecipitates
  6. filtrationwere collected by filtration
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-962deeaf5f974cf1849206e7809b0dc2
Source dataset
uspto-grants-1989_02
Patent number
US04808711

Reaction notes

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