4'-Mercaptoacetanilide → HCID 70571350, compound

HRID 1680643Notes

Reaction equation

[O:1]=[C:2]1[N:8]2[C@H:4]([O:5][C:6]([CH:9]=[CH2:10])=[CH:7]2)[CH2:3]1.[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)(=[O:13])[CH3:12]>>[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH2:10]/[CH:9]=[C:6]2/[CH2:7][N:8]3[C@H:4]([O:5]/2)[CH2:3][C:2]3=[O:1])=[CH:17][CH:16]=1)(=[O:13])[CH3:12]

Participants

Reactant 2

HCID 707774'-Mercaptoacetanilide

HCID 22807221HCID 22807221, compound

Product 1

HCID 70571350HCID 70571350, compound

Procedure

(5R)-7-Oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0]hept-2-ene (2.6 mmole) and p-acetamidophenyl mercaptan (0.5 g) were converted into the title compound using the process described in Example 1. The title compound was obtained as a colourless gum (102 mg), [α]D25 =+39.3° (c 1.0, CHCl3), (Found: M+ ; 304.0896; C15H16N2O3S requires 304.0882). νmax (CHCl3): 3380, 3280, 1790, 1720, 1690 (sh), 1665, 1590, 1496 cm-1. δ(CDCl3): 2.08 (3H, s), 2.60-3.50 (5H, complex), 4.18 (1H, d, J 14 Hz), 4.35 (1H, t, J 7 Hz), 5.30 (1H, d, J 2 Hz), 7.10-7.40 (4H, complex), 7.80 (1H, br.s). m/e: 304 (M+, 12%), 138 (100), 96 (62).

Sources & evidence

ORD record: ord-6ac00742d2a840f6904740744f87ce53
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04275067

Reaction notes

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