(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (R)-6-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2105444Notes

Reaction equation

HRID 2105444 reaction equation
C(N1CCC(OC2C=CC3N4CCCNC(=O)C4=CC=3C=2)CC1)(C)C.[CH2:26]([O:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([O:40][CH:41]1[CH2:46][CH2:45][N:44]([CH:47]([CH3:49])[CH3:48])[CH2:43][CH2:42]1)=[C:35]([Br:50])[CH:34]=2)=[O:30])[CH3:27].[C:51]([O:55][C:56]([N:58]1[CH2:62][C@H:61]([CH3:63])OS1(=O)=O)=[O:57])([CH3:54])([CH3:53])[CH3:52].CC(C)([O-])C.[K+]>>[CH2:26]([O:28][C:29]([C:31]1[N:32]([C@H:61]([CH3:63])[CH2:62][NH:58][C:56]([O:55][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:57])[C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([O:40][CH:41]1[CH2:46][CH2:45][N:44]([CH:47]([CH3:49])[CH3:48])[CH2:43][CH2:42]1)=[C:35]([Br:50])[CH:34]=2)=[O:30])[CH3:27]

Participants

5

Reactant 4

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 166797019-(1-Isopropyl-piperidin-4-yloxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-oneHCID 23665647Potassium tert-butoxideHCID 670179296-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 68467114(R)-6-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl esterYield 53%

Procedure

The title compound was synthesized in analogy to example 1, intermediate b), from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester, (S)-5-methyl-2,2-dioxo[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (prepared according to WO 02/010169) and potassium tert-butoxide, to give the desired compound as a light yellow oil (53%). The thus obtained crude product was used without further purification for the next step.

Sources & evidence

ORD record
ord-546a266cae1046189252497fde893d00
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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