Sodium Hydroxide → HCID 53998408, compound

HRID 2419872Notes

Reaction equation

HRID 2419872 reaction equation
[I-].[C:2]1([CH:8]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[O:9][C:10]([C:12]2[N:17]3[C:18](=[O:29])[C@@H:19]([NH:20][C:21](=[O:28])[CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[C@H:16]3[S:15][CH2:14][C:13]=2[CH2:30][P+:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O.O>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:29])[N:17]2[C:12]([C:10]([O:9][CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:11])=[C:13]([CH:30]=[P:31]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:14][S:15][C@H:16]12)=[O:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 88802658HCID 88802658, compound

Product 1

HCID 53998408HCID 53998408, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of [4-diphenylmethoxycarbonyl-7β-(2-thienylacetamido)ceph-3-em-3-ylmethyl] triphenylphosphonium iodide (25 g.) in acetone (300 ml.) with water (40 ml.) was cooled to 0° and taken to pH 11 with 2N-sodium hydroxide. The mixture, containing a precipitated yellow solid, was diluted with acetone (200 ml.) and water (50 ml.), and filtered. The collected solid was washed with acetone and ether, and dried in vacuo to give diphenylmethyl 7β-(2-thienylacetamido)-3-(triphenylphosphoranylidenemethyl)ceph-3-em-4-carboxylate (17 g., 78.5%) as a yellow crystalline solid, m.p. 133°-138° (Decomp), [α]D - 35° (CHCl3), λmax (CHCl3) 388 nm. (ε 18,500), 273 nm (ε6,240) and 267 nm (ε6,940), νmax (CHBr3) 3360 (NH), 1746 (β-lactam), 1670 (CO2R), 1642 and 1500 (CONH), and 1438 (P-C aryl) cm-1 ; τ(CDCl3) 4.82 (C(7) --H, dd, J 4.5, 9Hz), 4.95 (C(6) --H,d, J 4.5 Hz), 7.11 and 7.55 (C(2) --CH2, two dd. J 14 Hz., JP-H 1-2 Hz) and 4.5 ##STR34## [Found: C, 66.6; H, 4.7, N, 2.9; P, 3.9; S, 7.8. C45H37N2O4S2P (764.8) requires C, 70.6; H, 4.8; N, 3.6; P, 4.0; S, 8.4%[.

Workup

  1. additionThe mixture, containing a precipitated yellow solid
  2. filtrationfiltered
  3. washThe collected solid was washed with acetone and ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4e11eebe87264ee6a2750f07f7604db1
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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