Triethylamine → (6R,7R)-3-[(1-acetamidotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 483029Notes

Reaction equation

HRID 483029 reaction equation
[NH2:1][C@@H:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[N:15]([NH:16][C:17](=[O:19])[CH3:18])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[C:32]([NH:51][C:52]1[S:53][CH:54]=[C:55](/[C:57](=[N:70]/[O:71][CH3:72])/[C:58](ON2C3C=CC=CC=3N=N2)=[O:59])[N:56]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([NH:51][C:52]1[S:53][CH:54]=[C:55](/[C:57](=[N:70]/[O:71][CH3:72])/[C:58]([NH:1][C@@H:2]2[C:23](=[O:24])[N:4]3[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]4[N:15]([NH:16][C:17](=[O:19])[CH3:18])[N:14]=[N:13][N:12]=4)[CH2:7][S:8][C@H:3]23)=[O:59])[N:56]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 704535287beta-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acidHCID 88675991benzotriazol-1-yl (2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate

Product 1

HCID 13261994(6R,7R)-3-[(1-acetamidotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7β-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (0.450 g, 1.21 mmol), triethylamine (0.245 mg, 2.42 mmol) and dichloromethane (10 ml) was stirred at room temperature for 10 minutes. To the mixture was added 1-benzotriazolyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetate (0.678 g, 1.21 mmol) and allowed to react at 5° C. for 17 hours. The dichloromethane was removed by evaporation. Water (10 ml) and triethylamine (0.5 ml) were added to the residue. The aqueous layer was separated, washed with ethyl acetate (5 ml) and adjusted to pH 3.5 with citric acid. Precipitated substance was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. The residue was treated with ether and filtered to give pale yellow powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem- 4-carboxylic acid (0.790 g, 92%), mp 167°-170° C. (decomposition).

Workup

  1. customto react at 5° C. for 17 hours
  2. customThe dichloromethane was removed by evaporation
  3. additionWater (10 ml) and triethylamine (0.5 ml) were added to the residue
  4. customThe aqueous layer was separated
  5. washwashed with ethyl acetate (5 ml)
  6. customPrecipitated substance
  7. extractionwas extracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. additionThe residue was treated with ether
  12. filtrationfiltered

Sources & evidence

ORD record
ord-0848abbdd3bc4e1da1c4109145d7ec52
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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