(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → HCID 86622358, compound

HRID 501741Notes

Reaction equation

HRID 501741 reaction equation
C(O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)C=C.[CH2:19]([O:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([Br:32])=[CH:29][CH:30]=2)[C@@H:25]([NH2:33])[CH2:24]1)[CH:20]=[CH2:21].[O:34]1[CH2:36][C@@H:35]1[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:19]([O:22][C@H:23]1[C:31]2[C:26](=[CH:27][C:28]([Br:32])=[CH:29][CH:30]=2)[C@@H:25]([NH:33][CH2:36][C@@H:35]([OH:34])[C@@H:37]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:50])([CH3:49])[CH3:51])[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:24]1)[CH:20]=[CH2:21]

Participants

4

Reactant 3

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 59423731(1S,3R)-3-(Allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-amineHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine2×

Product 1

HCID 86622358HCID 86622358, compoundYield 82%

Procedure

Step BD (1). (1S,3R)-3-(Allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-amine from Step Z(1) was reacted with tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (Aldrich) according to the procedures described in Step V (1) to afford, after purification, 275 mg (82% yield) of tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate. MS (M+H)+ 531.43. 1H NMR (500 MHz, CDCl3) δ ppm 1.36 (s, 9H) 1.82 (ddd, J=12.67, 6.26, 6.10 Hz, 1H) 2.69-2.79 (m, 3H) 2.87 (dd, J=13.89, 8.09 Hz, 1H) 3.03 (dd, J=14.04, 4.58 Hz, 1H) 3.38-3.46 (m, 1H) 3.79 (s, 1H) 4.01-4.05 (m, 2H) 4.06-4.15 (m, 2H) 4.54 (d, J=9.16 Hz, 1H) 4.75 (t, J=6.10 Hz, 1H) 5.19 (dd, J=10.38, 1.53 Hz, 1H) 5.31 (ddd, J=17.24, 3.20, 1.53 Hz, 1H) 5.94 (ddd, J=22.74, 10.53, 5.49 Hz, 1H) 7.18-7.32 (m, 7H) 7.40 (d, J=8.24 Hz, 1H) 7.50 (s, 1H).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-d41a5d1dcf804c6393ea6753d51b88e4
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

Loading…