tert-Butyl L-valinate → (S)-2-(phenoxathiine-2-sulfonylamino)-succinamic acid

HRID 1953397Notes

Reaction equation

HRID 1953397 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][C:58](=[O:60])[NH2:59])[NH2:56])(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:56][C@@H:55]([CH2:57][C:58]([NH2:59])=[O:60])[C:54]([OH:61])=[O:53])(=[O:35])=[O:34]

Participants

5

Reactant 4

HCID 114626tert-Butyl L-valinateHCID 6995006L-Asparagine tert-butyl esterHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 53837821(S)-2-(phenoxathiine-2-sulfonylamino)-succinamic 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)-asparagine-t-butyl ester, (S)-2-(phenoxathiine-2-sulfonylamino)-succinamic acid is obtained; mp 165-175° C.

Sources & evidence

ORD record
ord-285344e6aa9449ab895b66fb7d9f9060
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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