2-(Phenylmethyl)oxirane → HCID 44450675, compound

HRID 1510214Notes

Reaction equation

HRID 1510214 reaction equation
[CH:1]([C@H:14]1[NH:19][CH2:18][C@@H:17]([NH2:20])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[CH2:30][CH:22]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH:1]([C@H:14]1[NH:19][CH2:18][C@@H:17]([NH:20][CH2:30][C@@H:22]([OH:21])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 948262-(Phenylmethyl)oxiraneHCID 11140080HCID 11140080, compound

Product 1

HCID 44450675HCID 44450675, compoundYield 33%

Procedure

Compound 3 (0.075 g, 0.281 mmol) was reacted with S-(−)-2,3-epoxypropyl benzene (0.056 g, 0.422 mmol) (Procedure A) and was purified by flash column chromatography over silica gel using diethyl ether/MeOH/Et3N (90:10:0.2) to yield 4d (0.037 g, 33%). 1H NMR (400 MHz, CDCl3): δ 1.23-1.35 (2H, m, H-5), 1.41-1.49 (1H, m, H-4ax), 1.75-1.78 (1H, m, H-4eq), 2.36-2.41 (1H, dd, J=3.2 Hz, J=8.8 Hz, NHCH2), 2.66-2.84 (5H, m, H-2, NHCH2, Ph-CH2), 2.89-2.92 (1H, m, H-3eq), 3.23 (1H, dt, J=2.4 Hz, J=10.0 Hz, H-6ax), 3.75 (1H, d, J=10.0 Hz, (Ph)2CH) 3.78-3.85 (1H, m, and CH—OH), 7.12-7.31 (13H, m, ArH), 7.35-7.36 (2H, m, ArH). Optical rotation, [α]25D=(−) 49.3° (c 0.96, MeOH). Free base was converted into oxalate salt 206-209° C.

Workup

  1. customwas purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-57135e5ac22a41e08393caec2b8ee579
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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