2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 86654901, compound

HRID 391871Notes

Reaction equation

HRID 391871 reaction equation
C(NC1SC(S(Cl)(=O)=O)=C(C)N=1)(=O)C.C[O:16][C:17](=[O:78])[C@@H:18]([NH:32][C:33]([CH:35]1[CH2:44][C:43]2[CH:42]=[C:41]3[O:45][CH2:46][C@H:47]([C:49]4[CH:54]=[CH:53][C:52]([O:55][CH2:56][C:57]5[CH:62]=[CH:61][C:60]([Cl:63])=[C:59]([Cl:64])[CH:58]=5)=[CH:51][CH:50]=4)[O:48][C:40]3=[CH:39][C:38]=2[CH2:37][N:36]1[S:65]([C:68]1[S:72][C:71]([NH:73]C(=O)C)=[N:70][C:69]=1[CH3:77])(=[O:67])=[O:66])=[O:34])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>>[NH2:73][C:71]1[S:72][C:68]([S:65]([N:36]2[CH:35]([C:33]([NH:32][C@@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[C:17]([OH:78])=[O:16])=[O:34])[CH2:44][C:43]3[CH:42]=[C:41]4[O:45][CH2:46][C@H:47]([C:49]5[CH:54]=[CH:53][C:52]([O:55][CH2:56][C:57]6[CH:62]=[CH:61][C:60]([Cl:63])=[C:59]([Cl:64])[CH:58]=6)=[CH:51][CH:50]=5)[O:48][C:40]4=[CH:39][C:38]=3[CH2:37]2)(=[O:67])=[O:66])=[C:69]([CH3:77])[N:70]=1

Participants

3

Reactant 2

HCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 86654902HCID 86654902, compound

Product 1

HCID 86654901HCID 86654901, compoundYield 46.5%

Procedure

The methyl ester hydrochloride salt (36 mg) was reacted with 2-acetylamino-4-methyl thiazole-5-sulfonyl chloride (26 mg) according to General Procedure E. The resulting (S)-2-({(S)-7-(2-acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-biphenyl-4-yl-propionic acid methyl ester (32 mg) was hydrolyzed according to General Procedures N and B to give the title compound (14 mg). LCMS: (m/z) 887.

Sources & evidence

ORD record
ord-3f2cf97b3f804a068cb2fecd545e3a02
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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