tert-Butyl ((S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate → methyl (3S,10R)-10-(3-chlorophenyl)-7-methyl-6-oxo-3-(((R)-tetrahydro-2H-pyran-3-yl)methyl)-11-oxa-2,5,7-triazatridecan-13-ylcarbamate

HRID 426074Notes

Reaction equation

HRID 426074 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19])[CH2:9][CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][CH:7]=1.NC[C@@H:23]([NH:32][C:33](=[O:39])OCCCC)[CH2:24][C@H:25]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27][CH2:26]1.[NH2:40][CH2:41][C@@H](N(C)C(=O)OC(C)(C)C)C[C@H]1CCCOC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19])[CH2:9][CH2:10][N:11]([CH3:12])[C:33](=[O:39])[NH:32][CH2:23][C@H:24]([CH2:25][C@H:31]2[CH2:30][CH2:29][CH2:28][O:27][CH2:26]2)[NH:40][CH3:41])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 58011482tert-Butyl ((S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamateHCID 66704449(R)-methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamateHCID 86642389butyl (S)-1-amino-3-((R)-oxepan-3-yl)propan-2-ylcarbamate

Product 1

HCID 25133025methyl (3S,10R)-10-(3-chlorophenyl)-7-methyl-6-oxo-3-(((R)-tetrahydro-2H-pyran-3-yl)methyl)-11-oxa-2,5,7-triazatridecan-13-ylcarbamate

Procedure

The following compounds were prepared following procedures analogous to those described in Example 21 using (R)-methyl 2-(1-(3-chlorophenyl)-3-(methylamino)propoxy)ethylcarbamate and ten-butyl (S)-1-amino-3-((R)-oxepan-3-yl)propan-2-ylcarbamate and tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate in Step 1. LC-MS (3 min) tR=1.2 m/z=500. 1H NMR (CD3OD) d 7.35-7.23 (m, 4H), 4.28 (dd, J=8.4, 4.4 Hz, 1H), 3.86-3.81 (m, 2H), 3.62 (s, 3H), 3.54 (br d, J=14.4 Hz, 1H), 3.50-3.23 (m, 10H), 3.14 (dd, J=11.2, 9.6 Hz, 1H), 2.90 (s, 3H), 2.74 (s, 3H), 1.95-1.43 (m, 8H), 1.26 (m, 1H).

Workup

  1. customThe following compounds were prepared
  2. customLC-MS (3 min) tR=1.2 m/z=500

Sources & evidence

ORD record
ord-c68b64b0974c47e2bea7df8689c9649f
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

Loading…