HCID 22807221, compound → HCID 70570162, compound

HRID 1680644Notes

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.[CH2:11]([O:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([O:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([S:28][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:26][CH:27]=1)=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 22807221HCID 22807221, compound

HCID 23455337HCID 23455337, compound

Product 1

HCID 70570162HCID 70570162, compound

Procedure

(5R)-7-Oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0]hept-2-ene (2.4 mmole) and p-benzyloxycarbonylaminophenyl mercaptan (0.775 g) were converted into the title compound using the process described in Example 1. The title compound was obtained as a colourless gum (63 mg), [α]D25 =34.6° (c 1.0, CHCl3), (Found: M+, 396.1136; C21H20N2O4S requires 396.1144). νmax (CHCl3): 3370, 3240, 1790, 1735, 1700, 1590, 1515 cm-1. δ(CDCl3): 2.71 (1H, d, J 16 Hz), 3.10-3.60 (4H, complex), 4.22 (1H, d, J 15 Hz), 4.38 (1H, t, J 7 Hz), 5.16 (2H, s), 5.32 (1H, d, J 2 Hz), 6.90 (1H, br.s), 7.10-7.45 (9 H, complex). m/e: 396 (M+, 6%), 138 (41), 108(20), 107(12), 96(46), 91(100).

Sources & evidence

ORD record: ord-077c2f6021ee4819afc1232c67203b1f
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04275067

Reaction notes

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