HCID 59364360, compound → HCID 25131638, compound

HRID 426072Notes

Reaction equation

HRID 426072 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][O:8][C@@H:9]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=1)[CH2:10][CH2:11][N:12]([CH3:34])[C:13](=[O:33])[NH:14][C@@H:15]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:16][N:17](C)[C:18](=O)OC(C)(C)C)=[O:4]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:41][C:37]1[CH:36]=[C:35]([C@H:9]([O:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[O:2][CH3:1])[CH2:10][CH2:11][N:12]([CH3:34])[C:13](=[O:33])[NH:14][C@@H:15]([CH2:26][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:16][NH:17][CH3:18])[CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 1

HCID 59364360HCID 59364360, compound

Product 1

HCID 25131638HCID 25131638, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl (S)-2-(3-((R)-3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-methylureido)-3-cyclohexylpropyl(methyl)carbamate (40 mg) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (5 mL). The reaction mixture was concentrated in vacuo. The residue was purified by Preparative HPLC to afford isomer 1 methyl (4S,10R)-10-(3-chlorophenyl)-4-(cyclohexylmethyl)-7-methyl-6-oxo-11-oxa-2,5,7-triazatridecan-13-ylcarbamate (8.88 mg, 27%) LC-MS (3 min) tR=2.195 m/z=497. 1H NMR (CD3OD) d 0.99 (m, 2H), 1.54 (m, 1H), 1.70 (m, 4H), 1.87 (m, 3H), 2.73 (s, 3H), 2.94 (s, 3H), 3.09 (m, 1H), 3.63 (s, 3H), 4.26 (m, 2H), 7.29 (m, 4H). isomer 1 methyl (4S,10R)-10-(3-chlorophenyl)-4-(cyclohexylmethyl)-7-methyl-6-oxo-11-oxa-2,5,7-triazatridecan-13-ylcarbamate and isomer 2 methyl (4S,10S)-10-(3-chlorophenyl)-4-(cyclohexylmethyl)-7-methyl-6-oxo-11-oxa-2,5,7-triazatridecan-13-ylcarbamate. LC-MS (3 min) tR=2.149 m/z=497. 1H NMR (CD3OD) d 0.96 (m, 2H), 1.25 (m, 5H), 1.54 (m, 1H), 1.69 (m, 4H), 1.89 (m, 3H), 2.71 (s, 3H), 2.93 (s, 3H), 3.06 (m, 1H0, 3.64 (s, 3H), 4.14 (m, 1H), 4.30 (m, 1H), 7.31 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by Preparative HPLC

Sources & evidence

ORD record
ord-818c0bec554447e39cb188e95a2d93e5
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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