Lithium hydroxide, monohydrate → HCID 68283607, compound

HRID 1527581Notes

Reaction equation

HRID 1527581 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([F:11])=[C:6]([CH2:12][NH:13][C:14]([C@@H:16]2[CH2:20][C@@H:19]([F:21])[CH2:18][N:17]2[C:22](=[O:36])[CH2:23][N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]([C:33](=[O:35])[CH3:34])=[CH:25]2)=[O:15])[CH:5]=1.O[Li].O>C1COCC1.CO.O>[C:33]([C:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:24]([CH2:23][C:22]([N:17]2[CH2:18][C@H:19]([F:21])[CH2:20][C@H:16]2[C:14]([NH:13][CH2:12][C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([Cl:10])[C:7]=2[F:11])[C:3]([OH:37])=[O:2])=[O:15])=[O:36])[CH:25]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68284416HCID 68284416, compound

Product 1

HCID 68283607HCID 68283607, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To 3-[({(2S,4R)-1-[2-(3-acetyl-indol-1-yl)-acetyl]-4-fluoro-pyrrolidine-2-carbonyl}-amino)-methyl]-5-chloro-4-fluoro-benzoic acid methyl ester Example 523 (35.0 mg, 0.066 mmol) in THF-MeOH—H2O (ratio 2:1:1; 1 mL) was added LiOH.H2O (2.76 mg, 0.066 mmol). The reaction mixture was stirred at RT for 4 h. Volatiles were evaporated and the residue was taken up in water, Acidification to pH=1 by addition of a 6M HCl solution formed a precipitate which was filtered and dried at 50° C. in vacuo for 1 h to afford the title compound as a solid. MS: 518.0 [M+H]+; tR (HPLC conditions c): 4.26 min.

Workup

  1. customVolatiles were evaporated
  2. additionAcidification to pH=1 by addition of a 6M HCl solution
  3. customformed a precipitate which
  4. filtrationwas filtered
  5. customdried at 50° C. in vacuo for 1 h

Sources & evidence

ORD record
ord-adfefb762d4d45e3bee0731d30b29bc2
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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