Benzoyl chloride → HCID 89615783, compound

HRID 1747740Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C@@H:11]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[C:20](=[O:33])[O:21][C:22]([CH2:29][CH:30]([CH3:32])[CH3:31])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH2:15]1)=[O:13]>>[CH2:29]([C:22]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[CH2:15][N:14]([C:12](=[O:13])[C@@H:11]([NH:10][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:19][CH2:18][C:17]=2[C:20](=[O:33])[O:21]1)[CH:30]([CH3:32])[CH3:31]

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 89628597HCID 89628597, compound

Product 1

HCID 89615783HCID 89615783, compound

Procedure

The procedure described for R06039-427 was employed to convert benzoyl chloride (6 mg, 0.041 mmol) to 5-((S)-2-amino-3-phenylpropanoyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (16 mg, 0.037 mmol) to provide N-((2S)-1-(3-isobutyl-1-oxo-3-phenyl-6,7-dihydrofuro[3,4-c]pyridin-5 (1H,3H,4H)-yl)-1-oxo-3-phenylpropan-2-yl)benzamide. The desired product was purified by column chromatography (4 g, SiO2, 0 to 100% dichloromethane/diethylether in hexanes) and isolated as a colorless oil (13 mg, 69%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.76-0.95 (m, 6H), 1.46-1.92 (m, 4H), 2.06-2.39 (m, 2H), 2.99-3.37 (m, 2H), 3.40-3.62 (m, 1H), 3.82-4.07 (m, 1H), 4.60 (d, J=19.59 Hz, 1H), 5.15-5.30 (m, 1H), 5.31-5.50 (m, 1H), 6.94-7.57 (m, 13H), 7.70-7.85 (m, 2H); MS m/z 523 (M+H)+, 521 (M−H)−.

Sources & evidence

ORD record: ord-199dc63f721f43aaa0315aab8aeae2d8
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150582B2

Reaction notes

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