Water → HCID 50997474, compound

HRID 1911852Notes

Reaction equation

HRID 1911852 reaction equation
[Si]([O:8][C@H:9]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:33])[N:23]([CH3:32])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:18][CH:17]=2)[N:11]1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C.C(O)(C(F)(F)F)=O.O>C(#N)C>[OH:8][C@H:9]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@@H:10]1[NH:11][C@H:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([N:23]([CH3:32])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[O:33])=[CH:20][CH:21]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86670468HCID 86670468, compound

Product 1

HCID 50997474HCID 50997474, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-{methyl[2-(pyridine-2-yl)ethyl]carbamoyl}benzyl)pyrrolidine-1-carboxylate was dissolved in a 3:3:1 mixture of acetonitrile (1.4 mL):TFA (1.4 mL):water (0.47 mL), and the mixture was heated to 55° C. and stirred for 1 hour. The mixture was then concentrated in vacuo and purified by mass directed reverse phase HPLC using acetonitrile/water with 0.1% NH4OH buffer. Lyophilization of the desired fractions gave the title compound (21 mg, 26% yield over three steps) as a brown oil.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. custompurified by mass

Sources & evidence

ORD record
ord-3bc828ddfc324829b0f2844814ec54c5
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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