HCID 10131699, compound → (2R,3S)-1-((1S,3R)-3-(allyloxy)cyclopentylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol

HRID 501693Notes

Reaction equation

HRID 501693 reaction equation
C(O[C@@H]1CC[C@H](N)C1)C=C.FC1C=C(C[C@H](NC(=O)OCC2C=CC=CC=2)[C@H]2CO2)C=C(F)C=1.[CH2:35]([O:38][C@H:39]1[CH2:43][CH2:42][C@@H:41]([NH:44][CH2:45][C@@H:46]([OH:68])[C@@H:47]([NH:57]C(=O)OCC2C=CC=CC=2)[CH2:48][C:49]2[CH:54]=[C:53]([F:55])[CH:52]=[C:51]([F:56])[CH:50]=2)[CH2:40]1)[CH:36]=[CH2:37].C(O[C@@H]1CC[C@H](NC[C@@H](O)[C@@H](NC(=O)OCC2C=CC=CC=2)CC2C=C(F)C=C(F)C=2)C1)C=C>>[CH2:35]([O:38][C@@H:39]1[CH2:43][CH2:42][C@H:41]([NH:44][CH2:45][C@@H:46]([OH:68])[C@@H:47]([NH2:57])[CH2:48][C:49]2[CH:54]=[C:53]([F:55])[CH:52]=[C:51]([F:56])[CH:50]=2)[CH2:40]1)[CH:36]=[CH2:37]

Participants

5

Reactant 4

HCID 10131699HCID 10131699, compoundHCID 55284252HCID 55284252, compoundHCID 86622325benzyl (2S,3R)-4-((1R,3S)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamateHCID 86622326benzyl (2S,3R)-4-((1S,3R)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate

Product 1

HCID 59423773(2R,3S)-1-((1S,3R)-3-(allyloxy)cyclopentylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-olYield 51%

Procedure

Step Y (3): Racemic cis-3-(allyloxy)cyclopentanamine from step Y (2) was reacted with benzyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate according to the conditions described in Step V (1). Purification by silica gel column chromatography provided 726 mg (51% yield) of a mixture of benzyl (2S,3R)-4-((1R,3S)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate and benzyl (2S,3R)-4-((1S,3R)-3-(allyloxy)cyclopentylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate. LC-MS (M+H)+=475.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.61-1.92 (m, 3H) 1.93-2.30 (m, 3H) 2.72 (dd, J=13.89, 10.83 Hz, 1H) 3.00 (d, J=9.16 Hz, 1H) 3.18 (t, J=14.34 Hz, 1H) 3.31-3.48 (m, 1H) 3.55-4.18 (m, 5H) 4.39 (dd, J=36.01, 4.88 Hz, 1H) 4.91-5.07 (m, 2H) 5.10-5.31 (m, 2H) 5.43 (dd, J=15.87, 8.55 Hz, 1H) 5.77-5.94 (m, 1H) 6.55-6.81 (m, 3H) 7.00-7.51 (m, 7H).

Workup

  1. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-73cb6824e4c14e48816cfcde5ed18aa8
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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