(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 501753Notes

Reaction equation

HRID 501753 reaction equation
FC(F)(F)C([NH:5][C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:15])[CH:13]=2)[C@@H:8]([OH:16])[CH2:7]1)=O.[O:19]1[CH2:21][C@@H:20]1[C@@H:22]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:38](O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)[CH:39]=[CH2:40]>>[CH2:40]([O:16][C@H:8]1[C:9]2[C:14](=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C@@H:6]([NH:5][CH2:21][C@@H:20]([OH:19])[C@@H:22]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7]1)[CH:39]=[CH2:38]

Participants

4

Reactant 3

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amineHCID 59423834HCID 59423834, compound

Product 1

HCID 86622364tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamateYield 86%

Procedure

Step BK (3): The product from Step BK (2) was reacted with tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (271 mg, 1.03 mmol) following a procedure analogous to Step AW (1) to afford 415 mg (86% yield) of tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-methyl-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate. LC-MS (M+H)+=467.29; 1H NMR (500 MHz, CDCl3) δ ppm 7.39-7.16 (m, 7H) 5.93-5.87 (m, 1H) 5.33-4.60 (m, 8H) 4.08 (d, 2H) 3.94 (m, 1H) 3.62 (m, 1H) 3.46 (d, 1H) 3.10-3.06 (m, 2H) 3.6 (m, 1H) 2.59-2.54 (m, 2H) 2.37 (s, 3H) 1.25 (s, 9H).

Sources & evidence

ORD record
ord-9daa7317598c46029e3c1a2a7b49ba45
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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