Phosphorus oxychloride → HCID 70615283, compound

HRID 1763811Notes

Reaction equation

HRID 1763811 reaction equation
P(Cl)(Cl)([Cl:3])=O.C([NH:8][C@@H:9]1[C:27](=[O:28])[N:11]2[C:12]([C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])=[C:13]([CH2:16][S:17][CH3:18])[CH2:14][S:15][C@H:10]12)=O>CO.CCOCC>[ClH:3].[NH2:8][C@@H:9]1[C:27](=[O:28])[N:11]2[C:12]([C:19]([O:21][CH2:22][C:23]([Cl:25])([Cl:24])[Cl:26])=[O:20])=[C:13]([CH2:16][S:17][CH3:18])[CH2:14][S:15][C@H:10]12

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 88801791HCID 88801791, compound

Product 1

HCID 70615283HCID 70615283, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (0.5 ml. 5.47 mmole) was added dropwise over 3 min. to a stirred suspension of 2,2,2-trichloroethyl 7β-formamido-3-methylthiomethylceph-3-em-4-carboxylate (1.05 g., 2.5 mmole) in dry methanol (10 ml.). During the addition the starting material went into solution and the temperature of the mixture reached a maximum of ca.45°. After 1 min. a white solid came out of solution and the mixture rapidly set solid. The mixture was diluted with ether (10 ml.), stirred briefly and the product collected, washed with ether (ca. 25 ml.) and dried to furnish the title hydrochloride as a feathery white solid (941 mg., 88%), m.p. 169° to 172° (dec.) [α]D + 5.25°, λmax. (MeOH) 272.5 nm. (ε 6,640), νmax. ca. 2600 (N+H3), 1775 (azetidin-2-one) and 1720 cm-1 (CO2CH2CCl3), τ 4.69 (1H,d, J 5 Hz; C7 -H), 4.88 and 5.01 (2H,AB-q, J 12 Hz; CH2CCl3), 4.90 (1H,d, J 5 Hz; C6 -H), 6.14 and 6.39 (2H,AB-q,J17 Hz C2 -CH2), 6.23 (2H,s; CH2SCH3) and 7.97 (3H,s; SCH3) (Found: C, 31.2; H, 3.3; Cl, 33.0; N, 6.6; S, 15.0. C11H 14 Cl4N2O3S2 (428.2) requires C, 30.85, H, 3.3; Cl, 33.1; N, 6.55; S, 15.0%). Electrophoresis showed a single spot, RX 1.56 (X=cephalexin) which migrated towards the cathode and which gave a mauve colour upon spraying with 0.5% (W/V) ninhydrin in ethanol.

Workup

  1. additionDuring the addition the starting material
  2. custom45°
  3. customthe product collected
  4. washwashed with ether (ca. 25 ml.)
  5. customdried

Sources & evidence

ORD record
ord-0e5692239064417c83e633ebadd796e4
Source dataset
uspto-grants-1978_09
Patent number
US04113591

Reaction notes

Loading…