L-Alanine 1,1-dimethylethyl ester → (S)-2-(phenoxathiine-2-sulfonylamino)-propionic acid

HRID 1953393Notes

Reaction equation

HRID 1953393 reaction equation
C1C2SC3C(=CC=CC=3)SC=2C=CC=1S(Cl)(=O)=O.[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)C)[NH2:44])(C)(C)C.C(OC(=O)[C@H](C)N)(C)(C)C>>[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]([NH:44][C@@H:43]([CH3:45])[C:42]([OH:48])=[O:41])(=[O:35])=[O:34]

Participants

5

Reactant 4

HCID 89016L-Alanine 1,1-dimethylethyl esterHCID 114626tert-Butyl L-valinateHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 15487612(S)-2-(phenoxathiine-2-sulfonylamino)-propionic 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)-alanine-t-butyl ester, (S)-2-(phenoxathiine-2-sulfonylamino)-propionic acid is obtained as a white solid; mp 75-85° C.

Sources & evidence

ORD record
ord-fd4be9ba30f54c78ba0cc1427847e0b9
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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