tert-Butyl L-valinate → HCID 15487616, compound

HRID 1953396Notes

Reaction equation

HRID 1953396 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:67])[C@H:55]([CH2:57][C:58]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[NH:60][CH:59]=1)[NH2:56])(C)(C)C>>[NH:60]1[C:61]2[C:66](=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:58]([CH2:57][C@H:55]([NH:56][S:33]([C:20]2[CH:21]=[CH:22][C:23]3[O:24][C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:31][C:32]=3[CH:19]=2)(=[O:35])=[O:34])[C:54]([OH:67])=[O:53])=[CH:59]1

Participants

5

Reactant 4

HCID 114626tert-Butyl L-valinateHCID 7020175(S)-tert-Butyl 2-amino-3-(1H-indol-3-yl)propanoateHCID 15487617Thianthrene-2-sulfonyl chlorideHCID 15487618HCID 15487618, compound

Product 1

HCID 15487616HCID 15487616, 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 (L)-tryptophan-t-butyl ester, (S)-3-(1H-indol-3-yl)-2-(phenoxathiine-2-sulfonylamino)-propionic acid is obtained; mp 120-130° C.

Sources & evidence

ORD record
ord-8e55c4a643f04edbbe0e0977ab37532f
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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