2-(Methylamino)ethanol → (2S)-3-([1,1'-biphenyl]-4-ylsulfonyl)-N-{(1S)-3-[(2-hydroxyethyl)(methyl)-amino]-1-phenylpropyl}-1,3-thiazolidine-2-carboxamide

HRID 1964818Notes

Reaction equation

HRID 1964818 reaction equation
CS(O[CH2:6][CH2:7][C@H:8]([NH:15][C:16]([C@H:18]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:21][CH2:20][S:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)=O.[CH3:38][NH:39][CH2:40][CH2:41][OH:42]>>[C:29]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:28]=[CH:27][C:26]([S:23]([N:22]2[CH2:21][CH2:20][S:19][C@H:18]2[C:16]([NH:15][C@H:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][N:39]([CH2:40][CH2:41][OH:42])[CH3:38])=[O:17])(=[O:24])=[O:25])=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 60036776(3S)-3-({[(2S)-3-([1,1'-biphenyl]-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)-3-phenylpropyl methanesulfonate2×

Product 1

HCID 60036770(2S)-3-([1,1'-biphenyl]-4-ylsulfonyl)-N-{(1S)-3-[(2-hydroxyethyl)(methyl)-amino]-1-phenylpropyl}-1,3-thiazolidine-2-carboxamide

Procedure

Following the general method A as outlined in Example 16, starting from (3S)-3-({[(2S)-3-([1,1′-biphenyl]-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)-3-phenylpropyl methanesulfonate (Intermediate 9) and 2-(methylamino)ethanol, the title compound was obtained in 94.3% purity by HPLC.

Sources & evidence

ORD record
ord-1d272b8b52064c95bc1bdb7dc763156f
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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