Triethylamine → HCID 86738831, compound

HRID 355224Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH:6]([S:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:5][C:4]1=[O:27].C(N(CC)CC)C.[C:35](OC=O)(=[O:37])C>C(Cl)Cl>[CH:35]([O:1][CH2:2][C@H:3]1[C@H:6]([S:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:5][C:4]1=[O:27])=[O:37]

Participants

Conditions

Temperature: -10 °C

Procedure

To a cooled (ice-salt) stirred solution of 3-hydroxymethyl-4-triphenylmethylthio-2-azetidinone (1.76 g 4.7 mmol) in CH2Cl2 (10 ml) and triethylamine (2.6 g, 25 mmol) was added dropwise formic-acetic acid anhydride (1.76 g, 20 mmol). The mixture was stirred 20 min at -10° C. and 20 min at room temperature, followed by partition between water and CH2Cl2. Drying and concentration of organic phase gave an oil which crystallized from ether to give 1.7 g (94.4%) of the title compound as white solid, mp 143°-144° C.; 1Hmr (CDCl3) δ: 7.98 (1H, formyl) 7.3 (15H, s), 4.82 (1H, 4-H), 4.25 (2H, d, J=9 Hz) and 3.37 ppm (1H, m); ir (nujol) νmax : 1723, 1763, 1776 cm-1. ##STR832##

Workup

customby partition between water and CH2Cl2
customDrying
customconcentration of organic phase gave an oil which
customcrystallized from ether

Sources & evidence

ORD record: ord-955a49c5c0ce49f398f97f9d97006e24
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04378314

Reaction notes

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