1,2,5-Thiadiazolidine-2-carboxylic acid, 4,4-dimethyl-, 1,1-dimethylethyl ester, 1,1-dioxide → HCID 19774184, compound

HRID 1613633Notes

Reaction equation

HRID 1613633 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13]N3CC(C)(C)NS3(=O)=O)[CH:11]=2)[NH:6][CH:5]=1.[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33]([CH3:36])([CH3:35])[NH:32][S:31]1(=O)=O)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([NH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][N:32]3[S:31][N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[CH2:34][C:33]3([CH3:36])[CH3:35])[CH:11]=2)[NH:6][CH:5]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 100606681,2,5-Thiadiazolidine-2-carboxylic acid, 4,4-dimethyl-, 1,1-dimethylethyl ester, 1,1-dioxideHCID 10448821HCID 10448821, compound

Product 1

HCID 19774184HCID 19774184, compoundYield 84%

Procedure

The title compound was prepared in 84% yield from Intermediate 3 and 2-tert-butyloxycarbonyl-4,4-dimethyl-1,2,5-thiadiazolidine-1,1-dioxide using a similar method to that described for Example 18 (step 2); white foam; δH (250 MHz, CDCl3) 8.04 (1H, br s, indole N--H), 7.58 (1H, s, Ar--H), 7.32 (2H, s, Ar--H), 7.02 (1H, d, J=2.2 Hz, Ar--H), 4.59 (1H, br s, --NH--), 4.36 (2H, s, Ar--CH2N--), 3.59 (2H, s, --CH2 --), 3.45 (2H, br q, J=6.3 Hz, --CH2NH--), 2.94 (2H, t, J=6.3 Hz, Ar--CH2 --), 1.55 (9H, s, t-Bu), 1.43 (9H, s, t-Bu), 1.30 (6H, s, --CMe2); m/z (FAB) 523 (M+ +1).

Sources & evidence

ORD record
ord-8dddfcf1b1c84e84a9bafd05554af8b1
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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