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

HRID 1383126Notes

Reaction equation

HRID 1383126 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]([C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1)=[N:8][O:9][CH:10]([C:12](=[O:15])[NH:13][NH2:14])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[C:35]([O:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[O:48][C:49](=[O:51])[CH3:50])[C:42]([Cl:44])=[O:43])(=[O:37])[CH3:36].CCOCC>C(Cl)Cl.CO>[ClH:44].[C:1]([O:5][C:6](=[O:22])[C:7]([C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1)=[N:8][O:9][CH:10]([C:12](=[O:15])[NH:13][NH:14][C:42](=[O:43])[C:41]1[CH:45]=[CH:46][C:47]([O:48][C:49](=[O:51])[CH3:50])=[C:39]([O:38][C:35](=[O:37])[CH3:36])[CH:40]=1)[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 867427662-(2-Amino-1,3-thiazol-4-yl)-2-(1-carbazoylethoxyimino)acetic acid tert-butyl ester

Product 1

HCID 884939382-(2-Amino-1,3-thiazol-4-yl)-2-{1-[3-(3,4-diacetoxybenzoyl)carbazoyl]ethoxyimino}acetic acid tert-butyl ester.hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 10 ml of methylene chloride was suspended 0.659 g (2 mmole) of 2-(2-amino-1,3-thiazol-4-yl)-2-(1-carbazoylethoxyimino)acetic acid tert-butyl ester, and to the suspension was added 2.5 g (12.3 mmole) of N,O-bis(trimethylsilyl)acetamide to form a solution. To the ice-cooled solution was added 0.565 g (2.2 mmole) of 3,4-diacetoxybenzoic acid chloride and the mixture was stirred for 1.5 hours 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 1.05 g of 2-(2-amino-1,3-thiazol-4-yl)-2-{1-[3-(3,4-diacetoxybenzoyl)carbazoyl]ethoxyimino}acetic acid tert-butyl ester.hydrochloride. (Yield: 98.0%)

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-b05beb47a68b4a95bf5f40923cbfe1a8
Source dataset
uspto-grants-1989_02
Patent number
US04808711

Reaction notes

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