tert-Butyl L-valinate → (S)-4-methyl-2-(phenoxathiine-2-sulfonylamino)-pentanoic acid

HRID 1953395Notes

Reaction equation

HRID 1953395 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(OC(=O)[C@H](C(C)C)N)(C)(C)C.C([O:53][C:54](=[O:61])[C@H:55]([CH2:57][CH:58]([CH3:60])[CH3:59])[NH2:56])(C)(C)C>>[CH3:59][CH:58]([CH3:60])[CH2:57][C@H:55]([NH:56][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:54]([OH:61])=[O:53]

Participants

5

Reactant 4

HCID 114626tert-Butyl L-valinateHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 9930463(S)-4-methyl-2-(phenoxathiine-2-sulfonylamino)-pentanoic 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)-leucine-t-butyl ester, (S)-4-methyl-2-(phenoxathiine-2-sulfonylamino)-pentanoic acid is obtained; mp 120-130° C.

Sources & evidence

ORD record
ord-9dc02bb304834bfd8ee3770d8b00421d
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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