tert-Butyl L-valinate → (S)-4-methanesulfinyl-2-(phenoxathiine-2-sulfonylamino)-butyric acid

HRID 1953394Notes

Reaction equation

HRID 1953394 reaction equation
C1C2SC3C(=CC=CC=3)SC=2C=C[C:2]=1[S:15](Cl)(=O)=[O:16].[CH:19]1[C:32]2[S:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:24][C:23]=2[CH:22]=[CH:21][C:20]=1[S:33](Cl)(=[O:35])=[O:34].C([O:41][C:42](=[O:48])[C@H:43]([CH:45](C)[CH3:46])[NH2:44])(C)(C)C.C(OC(=O)[C@H](CCSC)N)(C)(C)C>>[CH3:2][S:15]([CH2:46][CH2:45][C@H:43]([NH:44][S:33]([C:20]1[CH:21]=[CH:22][C:23]2[O:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:31][C:32]=2[CH:19]=1)(=[O:35])=[O:34])[C:42]([OH:41])=[O:48])=[O:16]

Participants

5

Reactant 4

HCID 114626tert-Butyl L-valinateHCID 7010638Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 15487613(S)-4-methanesulfinyl-2-(phenoxathiine-2-sulfonylamino)-butyric acid

Procedure

When in the procedure of Example 1, Step (b), thianthrene-2-sulfonyl chloride is replaced by phenoxathiine-2-sulfonyl chloride and (L)-valine-t-butyl ester is replaced with (L)-methionine-t-butyl ester, (S)-4-methanesulfinyl-2-(phenoxathiine-2-sulfonylamino)-butyric acid is obtained as a white solid;

Sources & evidence

ORD record
ord-6bd0ad30024040d4bb9481e90c96e957
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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