Potassium Carbonate → HCID 178476467, compound

HRID 638321Notes

Reaction equation

HRID 638321 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[S:23][CH:24]=3)[C:15](=[O:52])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2].C(=O)([O-])[O-].[K+].[K+].[C:59]([O:62][CH:63](Br)[CH3:64])(=[O:61])[CH3:60]>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[CH:11]([C:12]([O:14][CH:63]([O:62][C:59](=[O:61])[CH3:60])[CH3:64])=[O:13])[N:10]2[C:15](=[O:52])[C@@H:16]([NH:17][C:18](=[O:51])/[C:19](=[N:45]\[O:46][CH2:47][CH:48]3[CH2:50][CH2:49]3)/[C:20]3[N:21]=[C:22]([NH:25][C:26]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[S:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 13279147HCID 13279147, compound

Product 1

HCID 178476467HCID 178476467, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(6R,7R)-3-Carbamoyloxymethyl-7-[(Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylic acid (1.1 g) was stirred with potassium carbonate (105 mg) in N,N-dimethylformamide (5 ml) with ice water cooling under nitrogen. After five minutes, 1-acetoxy-1-ethyl bromide (300 mg) was added. After one hour at ice-bath temperature and 2.5 hours at 21°, the mixture was partitioned between ethyl acetate and aqueous hydrochloric acid. The aqueous layer was extracted with more ethyl acetate and the combined organic layers were washed with brine, dried with magnesium sulphate and evaporated to a foam. This was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 70%) in petroleum ether (bp 40°-60°) to give the title compound (840 mg); νmax (CHBr3) 3583, 3403 (NH and NH2), 1785 (β-lactam), 1730 (ester and carbamate) and 1688 and 1513 cm-1 (amide); τ (CDCl3) includes 3.04 (NH and OCHCH3), 3.22 (thiazole proton), 4.19 and 4.70 (7-H and 6-H), 4.8 to 5.6 (3CH2 and NH2), and 5.90 (--CH2O).

Workup

  1. waitAfter one hour at ice-bath temperature and 2.5 hours at 21°
  2. customthe mixture was partitioned between ethyl acetate and aqueous hydrochloric acid
  3. extractionThe aqueous layer was extracted with more ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulphate
  6. customevaporated to a foam
  7. customThis was chromatographed on Sorbsil U30 (50 g) in ethyl acetate (10 to 70%) in petroleum ether (bp 40°-60°)

Sources & evidence

ORD record
ord-5028e0de8b11458589144e4b78c0bd2c
Source dataset
uspto-grants-1985_12
Patent number
US04560683

Reaction notes

Loading…