Triethylamine → HCID 66843305, compound

HRID 254078Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:50]=[CH:49][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:45]([O:47]C)=[O:46])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.CCN(CC)CC>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:25]=[CH:26][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:45]([OH:47])=[O:46])[CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:35])=[O:31])=[CH:49][CH:50]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl-L-phenylalaninate (20 mg, 0.029 mmol) was dissolved in 1.6 ml MeOH and 0.2 ml H2O. Et3N (0.2 ml, 1.44 mmol) was added and the mixture was stirred overnight. The mixture was heated to 80° C. for 7 h. The mixture was purified by preparative HPLC using a C8 column (25×300 mm). A gradient from 20% to 40% MeCN in 0.1 M ammonium acetate was used as mobile phase. The product fraction was concentrated and lyophilized to yield 7 mg (36%). M/z: 688.

Workup

customThe mixture was purified by preparative HPLC
concentrationThe product fraction was concentrated
customto yield 7 mg (36%)

Sources & evidence

ORD record: ord-fbfe5a7528da4cd9a92fc71a95f3a0b6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871998B2

Reaction notes

Loading…