Hexamethylphosphoramide → Benzhydryl 7-(2-thienylacetamido)-3-(4-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate

HRID 259396

반응식

HRID 259396 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:14]([CH2:17]Br)[CH2:15][S:16][C@H:11]12)=[O:8].CN(C)P(N(C)C)(N(C)C)=O.[OH:48][CH2:49][CH2:50][CH2:51][C:52]([O-:54])=[O:53].[Na+]>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:14]([CH2:17][O:54][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][OH:48])=[CH:15][S:16][C@H:11]12)=[O:8]

참가 물질

5

반응물 3

HCID 12679Hexamethylphosphoramide2회HCID 23663870Sodium OxybateHCID 70634766Benzhydryl 7-(2-thienylacetamido)-3-bromomethyl-3-cephem-4-carboxylate

생성물 1

HCID 131710853Benzhydryl 7-(2-thienylacetamido)-3-(4-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2.24 g. (3.8 mmol) of benzhydryl 7-(2-thienylacetamido)-3-bromomethyl-3-cephem-4-carboxylate in 20 ml. of hexamethylphosphoramide (HMPA) at 0° C. under nitrogen was added a suspension of 0.530 g. (4.2 mmol) of sodium 4-hydroxybutanoate in 25 ml. of HMPA. After stirring 1.5 hours, ethyl acetate was added, and the resulting solution was washed with water (5X) and brine and dried over anhydrous MgSO4. Evaporation in vacuo to dryness provided 2.12 g. of product which was combined with that of an identical reaction ran on a 1 mmol scale. The combined products were chromatographed on a silica gel column using a cyclohexane:ethyl acetate (1:2) eluant to provide 293 mg. of a mixture of the title product and the corresponding 3-cephem compound. For the title product: nmr (CDCl3) δ1.7-2.6 ##STR26## 3.55 (m, 2, CH2OH), 3.83 (s, 2, side chain CH2), 4.63 (bs, 1, --CH2OH), 5.0 (s, 1, C4 --H), 5.23 (d, 1, J = 4 Hz, C6 --H), 5.58 (dd, 1, J = 4 and 8 Hz, C7 --H), 6.42 (bs, 1, C2 --H), 6.95 (s, 1, ester CH), and 7.36 (m, 13, thienyl + ArH).

후처리

  1. additiona suspension of 0.530 g
  2. washthe resulting solution was washed with water (5X) and brine
  3. dry with materialdried over anhydrous MgSO4
  4. customEvaporation in vacuo to dryness
  5. customprovided 2.12 g
  6. customof an identical reaction
  7. customThe combined products were chromatographed on a silica gel column
  8. customto provide 293 mg

출처 및 근거

ORD 기록
ord-eaf780383c304188828ec1b9c6543e33
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04038275

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