Dimethylformamide → HCID 13279147, compound

HRID 638320Notes

Reaction equation

HRID 638320 reaction equation
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH:12]1([CH2:15][O:16]/[N:17]=[C:18](/[C:22]2[N:23]=[C:24]([NH:27][C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[S:25][CH:26]=2)\[C:19]([OH:21])=O)[CH2:14][CH2:13]1.[NH2:47][C@@H:48]1[C:63](=[O:64])[N:50]2[C:51]([C:60]([OH:62])=[O:61])=[C:52]([CH2:55][O:56][C:57](=[O:59])[NH2:58])[CH2:53][S:54][C@H:49]12>C(Cl)Cl.O.C(N(CC)CC)C>[C:57]([O:56][CH2:55][C:52]1[CH2:53][S:54][C@@H:49]2[C@H:48]([NH:47][C:19](=[O:21])/[C:18](=[N:17]\[O:16][CH2:15][CH:12]3[CH2:13][CH2:14]3)/[C:22]3[N:23]=[C:24]([NH:27][C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:25][CH:26]=3)[C:63](=[O:64])[N:50]2[C:51]=1[C:60]([OH:62])=[O:61])(=[O:59])[NH2:58]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 11391647HCID 11391647, compoundHCID 13269246HCID 13269246, compound

Product 1

HCID 13279147HCID 13279147, compoundYield 78.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Oxalyl chloride (0.37 ml.) was added to a solution of N,N-dimethylformamide (0.38 ml) in methylene chloride (10 ml) with stirring under nitrogen at -20°. After ten minutes with ice water cooling, the mixture was recooled to -20° and (Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (1.94 g) was added and the solution was stirred with ice-water cooling for 10 minutes. The solution was recooled to -20° and added to a solution of (6R,7R)-7-amino-3-carbamoyloxymethylceph-3-em-4-carboxylic acid (1.09 g) in industrial methylated spirits (12 ml) and water (3 ml) containing triethylamine (2.4 ml) at -10° and with vigorous stirring. After five minutes, the solution was partitioned between water and methylene chloride. Dilute hydrochloric acid was added to adjust the aqueous layer to pH >2. The aqueous layer was extracted with more methylene chloride and the combined organic layers were washed with water, dried with magnesium sulphate and evaporated. The residue was triturated with diethyl ether to give the title compound (2.32 g); [α]D21 +15.88° (c 0.69, CHCl3); νmax (Nujol) 3540 to 3100 (NH, NH2, OH, and water), 1785 (β-lactam), 1720 (acid and carbamate) and 1683 and 1510 cm-1 (amide).

Workup

  1. customwas recooled to -20°
  2. customwas recooled to -20°
  3. customthe solution was partitioned between water and methylene chloride
  4. additionDilute hydrochloric acid was added
  5. extractionThe aqueous layer was extracted with more methylene chloride
  6. washthe combined organic layers were washed with water
  7. dry with materialdried with magnesium sulphate
  8. customevaporated
  9. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-237bba098cd24ae3bcb45991440228dc
Source dataset
uspto-grants-1985_12
Patent number
US04560683

Reaction notes

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