1-Hydroxybenzotriazole → Methyl (2R)-3-{[4-({5-cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-YL}methyl)benzoyl]amino}-2-hydroxypropanoate

HRID 1669825Notes

Reaction equation

HRID 1669825 reaction equation
[CH:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=3)[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:44][CH2:45][C@@H:46]([OH:51])[C:47]([O:49][CH3:50])=[O:48].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:44][CH2:45][C@@H:46]([OH:51])[C:47]([O:49][CH3:50])=[O:48])=[O:19])=[CH:15][CH:14]=3)[N:10]=[C:9]([C:22]3[CH:23]=[CH:24][C:25]([O:28][C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 673350634-({5-Cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-yl}methyl)benzoic acidHCID 86590828(R)-methyl 3-amino-2-hydroxypropanoate hydrochloride

Product 1

HCID 67334317Methyl (2R)-3-{[4-({5-cyclohexyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-YL}methyl)benzoyl]amino}-2-hydroxypropanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 44.4 mg product from Step D Example 1, 28.8 mg EDC, 20.3 mg HOBt, 31.1 mg methyl (2R)-3-amino-2-hydroxypropanoate hydrochloride from Step C above and 70 μL DIEA in 1 mL DMF was stirred at room temperature over night. The title compound was isolated by preparative HPLC using 55˜75% MeCN gradient over 10 minutes at 8.0 mL per minute with 0.1% TFA on a 9.4×250 mm SB-C18 Zorbax column as a white solid after lyophilization. LC-MS: 2.55 min. (M+H=546.3).

Sources & evidence

ORD record
ord-8c4ed0bd51be43ab8d795b0fe92cc901
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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