1,2-Dichloroethane → (R)-3-[N-(5'-Chloro-2'-fluorobiphenyl-4-ylmethyl)-N'-(3-methoxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid 2,2,3,3,3-pentafluoropropyl Ester

HRID 541518Notes

Reaction equation

HRID 541518 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:32])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:26][C@@H:27]([OH:31])[C:28]([OH:30])=[O:29])[NH:16][C:17]([C:19]3[O:23][N:22]=[C:21]([O:24][CH3:25])[CH:20]=3)=[O:18])=[CH:10][CH:9]=2)[CH:7]=1.C(Cl)CCl.C1C=C2N=NN(O)C2=CC=1.O.C(Cl)Cl.[F:51][C:52]([F:59])([C:55]([F:58])([F:57])[F:56])[CH2:53]O.C(O)(C(F)(F)F)=O>>[F:51][C:52]([F:59])([C:55]([F:58])([F:57])[F:56])[CH2:53][O:29][C:28](=[O:30])[C@H:27]([OH:31])[CH2:26][N:15]([CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:32])=[CH:13][CH:12]=1)[NH:16][C:17]([C:19]1[O:23][N:22]=[C:21]([O:24][CH3:25])[CH:20]=1)=[O:18]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 98722,2,3,3,3-PentafluoropropanolHCID 27960291-Hydroxybenzotriazole hydrateHCID 67972936(R)-3-[N-(5'-Chloro-2'-fluorobiphenyl-4-ylmethyl)-N'-(3-methoxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic Acid

Product 1

HCID 86705096(R)-3-[N-(5'-Chloro-2'-fluorobiphenyl-4-ylmethyl)-N'-(3-methoxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid 2,2,3,3,3-pentafluoropropyl EsterYield 23%

Procedure

(R)-3-[N-(5′-Chloro-2′-fluorobiphenyl-4-ylmethyl)-N′-(3-methoxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid (20 mg, 43 μmol), EDC (40.16 mg, 0.2587 mmol), and HOBt hydrate (39.62 mg, 0.2587 mmol) were combined in DCM (0.5 mL, 8 mmol) and stirred at room temperature. After 10 minutes, 2,2,3,3,3-pentafluoro-1-propanol (51.8 mg, 345 μmol) was added. The resulting mixture was stirred at room temperature overnight to yield the title compound (5.9 mg, purity 100%) as a TFA salt. MS m/z [M+H]+ calc'd for C24H20ClF6N3O6, 596.09. found 596.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-af16e881ae4a49f68565f988ef6bb2cc
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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