(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191230Notes

Reaction equation

HRID 2191230 reaction equation
[O:1]([CH2:8][C@@H:9]1C[CH2:12][CH2:11][N:10]1[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27])(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C[C@@H]1CCN1C(OC(C)(C)C)=O)C1C=CC=CC=1>>[O:1]([CH2:8][C@@H:9]1[CH2:12][CH2:11][N:10]1[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27])(=[O:15])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 9821545(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 11565179(S)-tert-Butyl 2-(phenoxymethyl)azetidine-1-carboxylate

Product 1

HCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dioneYield 63%

Procedure

(S)-5-(2-Phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (17) was prepared according to the same procedure for compound 10, except using compound 16, and purified with ether to afford 715 mg (63%) of 17 as a yellow solid, mp 173.2-174.5° C. 1H NMR (300 MHz, DMSO) δ 11.48 (s, 1H), 7.98 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.77 (s, 1H), 7.27 (m, 2H), 7.10 (d, J=8.1 Hz, 1H), 6.91 (d, J=7.8 Hz, 3H), 4.20-4.02 (m, 3H), 3.70 (m, 1H), 3.55 (m, 1H), 2.22 (m, 1H), 2.02 (m, 1H). LRMS (FAB) m/e: 373.0 (M+H, 100). Anal. Calcd for C18H16N2O5S.0.5H2O: C, 56.68, H, 4.49; N, 7.34. Found: C, 56.96, H, 4.39; N, 7.30.

Workup

  1. custom(S)-5-(2-Phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (17) was prepared
  2. custompurified with ether

Sources & evidence

ORD record
ord-d5f55eb688bb428b9075a8d445ee810b
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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