Water → (S)-2-(3,5-Difluorophenyl)-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.07,11]docos-3-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate

HRID 751755Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:44]C(=O)OC(C)(C)C)[C:11](=[O:43])[NH:12][C@H:13]2[CH2:34][O:33][C:32](=[O:35])[C@H:31]3[N:27]([CH2:28][CH2:29][CH2:30]3)[C:26](=[O:36])[C@H:25]([CH3:37])[NH:24][C:23](=[O:38])[C@H:22]([CH3:39])[N:21]([CH3:40])[C:20](=[O:41])[C@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[C:14]2=[O:42])[CH:5]=[C:6]([F:8])[CH:7]=1.O.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>ClCCl>[F:53][C:54]([F:59])([F:58])[C:55]([O-:57])=[O:56].[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH3+:44])[C:11](=[O:43])[NH:12][C@H:13]2[CH2:34][O:33][C:32](=[O:35])[C@H:31]3[N:27]([CH2:28][CH2:29][CH2:30]3)[C:26](=[O:36])[C@H:25]([CH3:37])[NH:24][C:23](=[O:38])[C@H:22]([CH3:39])[N:21]([CH3:40])[C:20](=[O:41])[C@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[C:14]2=[O:42])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.12 g (2.94 mmol) of the carbamate from example 12A are dissolved in dichloromethane (32 ml) and cooled to 0° C. Subsequently, a mixture of water and trifluoroacetic acid (1/9) (32 ml) is added, and the mixture is stirred at 0° C. for 45 min. and then evaporated. 2.83 g of crude product are obtained, which after taking up in toluene and dichloromethane and subsequent concentration is reacted further.

Workup

additionis added
customevaporated

Sources & evidence

ORD record: ord-80877ab367bd40c48e07faaa3ad1852d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405201B2

Reaction notes

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