tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

HRID 501739Notes

Reaction equation

HRID 501739 reaction equation
[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:12]=2)[C@@H:7]([NH2:18])[CH2:6]1)[CH:2]=[CH2:3].[F:19][C:20]1[CH:21]=[C:22]([CH2:27][C@H:28]([NH:32]C(=O)OC(C)(C)C)[C@H:29]2[CH2:31][O:30]2)[CH:23]=[C:24]([F:26])[CH:25]=1>>[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:12]=2)[C@@H:7]([NH:18][CH2:31][C@@H:29]([OH:30])[C@@H:28]([NH2:32])[CH2:27][C:22]2[CH:23]=[C:24]([F:26])[CH:25]=[C:20]([F:19])[CH:21]=2)[CH2:6]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine3×

Product 1

HCID 59423712(2R,3S)-1-((1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-olYield 66%

Procedure

Step BA (1): (1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine (940 mg, 3.8 mmol, from Step AY (1)) was reacted with tert-butyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (1.0 g, 3.3 mmol) following a procedure analogous to Step AW (1) to afford, after purification, 1.2 g (66% yield) of (2R,3S)-1-((1S,3R)-3-(allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol. LC-MS (M+H)+=547.20. 1H NMR (300 MHz, CDCl3) δ 0.9-1.1 (t, 3H) 1.3 (s, 9H) 1.7-1.9 (m, 2H) 1.9-2.0 (m, 1H) 2.5-3.1 (M, 5H) 3.4-3.5 (m, 1H) 3.7-3.8 (m, 1H) 3.8-4.0 (t, 2H) 4.0-4.1 (m, 2H) 4.5-4.6 (m 1H) 4.7-4.8 (m, 1H) 5.1-5.4 (m, 2H) 5.8-6.0 (m, 1H) 6.5-6.9 (m, 5H) 7.2-7.3 (d, 1H).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-280b3a32e5d2482187868fb6659a9a54
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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