(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid → HCID 66723869, compound

HRID 1476327Notes

Reaction equation

HRID 1476327 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[N:25]([C:26](=[O:55])[CH2:27][C@@H:28]([NH:37][C:38]2[CH:43]=[CH:42][C:41]([S:44]([NH2:47])(=[O:46])=[O:45])=[CH:40][C:39]=2[S:48]([C:51]([F:54])([F:53])[F:52])(=[O:50])=[O:49])[CH2:29][S:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:24][CH2:23][O:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Si](OC[C@H]1COCCN1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C1(SC[C@H](NC2C=CC(S(=O)(=O)N)=CC=2S(C(F)(F)F)(=O)=O)CC(O)=O)C=CC=CC=1>>[Si:1]([O:18][CH2:19][C@@H:20]1[N:25]([C:26](=[O:55])[CH2:27][C@@H:28]([NH:37][C:38]2[CH:43]=[CH:42][C:41]([S:44]([NH2:47])(=[O:46])=[O:45])=[CH:40][C:39]=2[S:48]([C:51]([F:52])([F:54])[F:53])(=[O:49])=[O:50])[CH2:29][S:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:24][CH2:23][O:22][CH2:21]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 66723519(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid2×HCID 66723689HCID 66723689, compoundHCID 131732786HCID 131732786, compound2×

Product 1

HCID 66723869HCID 66723869, compoundYield 24%

Procedure

The title product (0.2 g, yield: 24%) was prepared using a procedure similar to the one described for the synthesis of INTERMEDIATE 104. (R)-3-((tert-Butyldiphenylsilyloxy)methyl)morpholine, hydrochloride salt (INTERMEDIATE 107, 0.200 g, 0.24 mmol) and (R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid (INTERMEDIATE 8, 0.500 g, 1.00 mmol) were used as starting material. The title product was purified by column chromatography (ISCO, eluting with 0→100% DCM/10% MeOH in DCM).

Workup

  1. customThe title product was purified by column chromatography (ISCO, eluting with 0→100% DCM/10% MeOH in DCM)

Sources & evidence

ORD record
ord-a107f1e257354696b5fedf01201305f0
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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