1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,5-Dioxopyrrolidin-1-yl 4-((3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy) propan-2-yl)-4-(tributylstannyl)benzyl)(methyl)amino)-4-oxobutanoate

HRID 926933Notes

Reaction equation

[F:1][C:2]([F:42])([F:41])[C:3]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][C:27]=1[Sn:28]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:15][N:16]([CH3:24])[C:17](=[O:23])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].O[N:44]1[C:48](=[O:49])[CH2:47][CH2:46][C:45]1=[O:50].CCN=C=NCCCN(C)C>C(#N)C>[F:42][C:2]([F:1])([F:41])[C:3]([C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][C:27]=1[Sn:28]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:15][N:16]([CH3:24])[C:17](=[O:23])[CH2:18][CH2:19][C:20]([O:22][N:44]1[C:48](=[O:49])[CH2:47][CH2:46][C:45]1=[O:50])=[O:21])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

Conditions

Temperature: 20 °C

Procedure

Compound 15 (170 mg, 236 mmol) was dissolved in acetonitrile (5 mL), N-hydroxysuccinimide (54 mg, 472 mmol) and EDCI (90 mg, 472 μmol) were added and the mixture stirred 6 h at 20° C. The solvent was removed under vacuum and the residue was purified over silica gel using dichloromethane/acetone (1/1) as eluant to give 155 mg (190 μmol, 80% yield) of a colorless oil.

Workup

customThe solvent was removed under vacuum
customthe residue was purified over silica gel

Sources & evidence

ORD record: ord-14a1a649a5834078b94e671f75dc3832
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290421B2

Reaction notes

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