tert-Butyl L-valinate → HCID 15487607, compound

HRID 1953392Notes

Reaction equation

HRID 1953392 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]([CH3:47])[CH3:46])[NH2:44])(C)(C)C.C(OC(=O)[C@@H](C(C)C)N)(C)(C)C>>[CH3:46][CH:45]([CH3:47])[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:48])=[O:41]

Participants

5

Reactant 4

HCID 114626tert-Butyl L-valinateHCID 6931638tert-butyl D-valinateHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 15487607HCID 15487607, compound

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 (D)-valine-t-butyl ester, (S)-3-methyl-2-(phenoxathiine-2-sulfonylamino)-butyric acid is obtained as an off-white solid; mp 171-175° C.

Sources & evidence

ORD record
ord-8b997e8d7277484fbe48d478b50f2aef
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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