Diethylamine → HCID 18391841, compound

HRID 617765Notes

Reaction equation

[CH2:1]([C:3]1([CH2:34][CH3:35])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14](O)[CH2:15][O:16][CH3:17])=[CH:10][CH:9]=2)[N:5]([C:19]([NH:21][C@H:22]([CH2:30][CH:31]=[CH2:32])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[O:20])[C:4]1=[O:33])[CH3:2].[Br-].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:57]([NH:59][CH2:60][CH3:61])[CH3:58]>>[CH2:34]([C:3]1([CH2:1][CH3:2])[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([N:59]([CH2:60][CH3:61])[CH2:57][CH3:58])[CH2:15][O:16][CH3:17])=[CH:10][CH:9]=2)[N:5]([C:19]([NH:21][C@H:22]([CH2:30][CH:31]=[CH2:32])[C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[O:20])[C:4]1=[O:33])[CH3:35]

Participants

Reactant 3

HCID 8021Diethylamine

HCID 12890784Triphenylphosphane dibromide

HCID 18391840HCID 18391840, compound

Product 1

HCID 18391841HCID 18391841, compound

Procedure

According to the procedure given in Example 21, Step D, 86 mg (0.18 mmol) of 3,3-diethyl-1-[(R)-α-(allyl)-4-(methyl)benzylaminocarbonyl]-4-(S)-[4-(1-(RS)-(hydroxy)-2-methoxyethyl) phenoxy]azetidin-2-one, 98 mg (0.23 mmol) of triphenylphosphine dibromide and ca. 0.3 mL of diethylamine gave after purification on 15 gm of silica eluting with 500 mL of 98:2 methylene chloride: methanol then 200 mL of 97.5:2.5 methylene chloride: methanol 44 mg (46%) of an oil.

Workup

customgave
customafter purification on 15 gm of silica eluting with 500 mL of 98:2 methylene chloride

Sources & evidence

ORD record: ord-6005565fd665411f9e6c7d85a2b36255
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952321

Reaction notes

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