Dimethylamine → HCID 11384295, compound

HRID 1784340Notes

Reaction equation

[C:1]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([C:24](=[O:27])[CH2:25][F:26])[CH2:20][C:21]([OH:23])=O)=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:28][NH:29][CH3:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C(OCC)(=O)C>[CH3:28][N:29]([CH3:30])[C:21](=[O:23])[CH2:20][CH:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[C:24](=[O:27])[CH2:25][F:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(CBz-Val-amido)-5-fluoro-4-oxo-pentanoic acid (150 mg, 0.39 mmol) in THF (5 ml) was added a solution of 2.0 M dimethylamine in THF (0.2 ml, 0.4 mmol), EDCI (82.2 mg, 0.42 mmol) and HOBT (106 mg, 0.78 mmol) at 0° C. The resulting mixture was stirred for 2 h at 0° C., then was stirred at room temperature overnight. The solution was diluted with ethyl acetate (20 ml), washed with water (4×20 ml), and the organic layer was dried and evaporated. The residue was purified by chromatography over silica gel (hexane-EtOAc, 1:1 to pure EtOAc) to give 10 mg (6%) of the titled compound as a white solid. 1H NMR (DMSO-d6): 8.36-8.30 (m, 1H), 7.45 (d, J=8.1 Hz, 1H), 7.33-7.29 (m, 5H), 5.45-5.09 (m, 2H), 5.03 (bs, 2H), 4.59-4.57 (m, 1H), 3.90-3.82 (m, 1H), 2.94 (bs, 3H), 2.84-2.73 (m, 4H), 1.97-1.93 (m, 1H), 1.25 (bs, 1H), 0.86-0.82 (m, 6H).

Workup

stirringwas stirred at room temperature overnight
washwashed with water (4×20 ml)
customthe organic layer was dried
customevaporated
customThe residue was purified by chromatography over silica gel (hexane-EtOAc, 1:1 to pure EtOAc)

Sources & evidence

ORD record: ord-b24b3951135941398bb6b1c74b84edca
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504382B2

Reaction notes

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