(S)-5-Chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1H-indole-2-carboxamide → Ethyl (S)-5-chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25]([N:28]1[CH2:33][CH2:32][O:31][CH:30]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29]1)(=[O:27])=[O:26].ClC1C=C2C(=CC=1)NC(C(N)=O)=C2S(N1CCO[C@H](COC2C=CC=CC=2)C1)(=O)=O.O(C[C@H]1OCCNC1)C1C=CC=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])=[O:13])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:5]2[S:25]([N:28]1[CH2:33][CH2:32][O:31][C@H:30]([CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29]1)(=[O:27])=[O:26]Participants
4
Reactant 3
Product 1
Procedure
The product from Step A of Example 22 was resolved by preparative chiral HPLC (ChiralPak AD) to produce a first-eluting enantiomer and a second-eluting enantiomer. To assign the (S)-configuration to the first-eluting enantiomer, (S)-2-(phenoxymethyl)morpholine (from resolution of the racemate by preparative ChiralPak AD HPLC) was converted to the titled product using the procedure described in Step A of Example 22. The configuration of (S)-2-(phenoxymethyl)morpholine was assigned by 1H NMR analysis of the derived Mosher's amide (cf. J. Org. Chem. 1996, 61, 2056-2064).
Workup
- customto produce a first-eluting enantiomer
Sources & evidence
- ORD record
- ord-a3c1d18fe84f44ff90d50193adf1f18f
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560546B2
Reaction notes
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