Hexane → HCID 178448368, compound

HRID 1030042Notes

Reaction equation

[CH2:1]([C:3]1([CH2:31][CH3:32])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=2)[N:5]([C:16]([NH:18][C@H:19]([CH2:27][CH2:28][CH3:29])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[O:17])[C:4]1=[O:30])[CH3:2].C1([P:39]([O:43]CC)[O:40][CH2:41][CH3:42])C=CC=CC=1.C(OCC)(=O)C.[CH3:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>>[CH2:1]([C:3]1([CH2:31][CH3:32])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:54]3[CH:53]=[CH:52][CH:57]=[CH:56][CH:55]=3)[PH:39]([O:40][CH2:41][CH3:42])=[O:43])=[CH:10][CH:9]=2)[N:5]([C:16]([NH:18][C@H:19]([CH2:27][CH2:28][CH3:29])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[O:17])[C:4]1=[O:30])[CH3:2]

Participants

Reactant 4

HCID 8058Hexane2×

HCID 8857Ethyl Acetate2×

HCID 74225Diethyl phenylphosphonite

HCID 18391849HCID 18391849, compound

Product 1

HCID 178448368HCID 178448368, compound

Conditions

Temperature: 80 °C

Procedure

A mixture of (4S)-3,3-diethyl-1-[(R)-α-n-propyl-(4-methyl)-benzylaminocarbonyl]-4-[4-(bromomethyl)phenoxy]-azetidin-2-one (203 mg, 0.40 mmol) and diethyl phenylphosphonite (155 μL, 0.81 mmol) was heated for 1 hour at 80° C. The desired product was obtained pure after flash chromatography on silica gel using initially 33% ethyl acetate in hexane and subsequently 50% ethyl acetate in hexane as the mobile phase; yield 223 mg (93%); FAB MS m/z 591 (M+1).

Sources & evidence

ORD record: ord-fd6c3360575f4665b3ea73976dcc404c
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104862

Reaction notes

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