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Lithium Hydroxide → HCID 89720667, compound

HRID 63752
Notes
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Reaction equation

HRID 63752 reaction equation
C([O:4][C:5](=[O:75])[C@@H:6]([NH:25][C:26](=[O:74])[C:27]1[C:32]([F:33])=[CH:31][C:30]([CH2:34][NH:35][CH2:36][C:37]2[CH:42]=[C:41]([F:43])[C:40]([C:44](=[O:71])[NH:45][C@H:46]([C:65]([O:67]CCC)=[O:66])[CH2:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]4[C:55](=[O:64])[N:56]([CH3:63])[C:57](=[O:62])[N:58]([CH3:61])[C:59]=4[CH3:60])=[CH:50][CH:49]=3)=[C:39]([F:72])[CH:38]=2)=[CH:29][C:28]=1[F:73])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)CC.C1COCC1.[Li+].[OH-]>O>[F:73][C:28]1[CH:29]=[C:30]([CH:31]=[C:32]([F:33])[C:27]=1[C:26](=[O:74])[NH:25][C@H:6]([C:5]([OH:75])=[O:4])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:34][NH:35][CH2:36][C:37]1[CH:42]=[C:41]([F:43])[C:40]([C:44]([NH:45][C@@H:46]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([C:54]3[C:55](=[O:64])[N:56]([CH3:63])[C:57](=[O:62])[N:58]([CH3:61])[C:59]=3[CH3:60])=[CH:50][CH:49]=2)[C:65]([OH:67])=[O:66])=[O:71])=[C:39]([F:72])[CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 89720749(S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl ester

Product 1

HCID 89720667HCID 89720667, compound
Yield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 200 mL flask containing (S)-2-[4-[[3,5-difluoro-4-[(S)-1-propoxycarbonyl-2-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]ethylcarbamoyl]benzylamino]methyl]-2,6-difluorobenzoylamino]-3-[4-[1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]phenyl]propionic acid propyl ester (1004 mmg, 0.97 mmol) was added THF (25 mL), water (25 mL) and LiOH (193 mg, 4.6 mmol) and the reaction stirred at room temperature overnight. The reaction was concentrated, dried from acetonitrile yielding a white solid that was mixed with DMSO (13 mL) and water (12 mL). This mixture was heated minimally, filtered and to the filtrate was added TFA (0.25 mL) resulting in a precipitate. The precipitate was diluted with water (50 mL), filtered, washed with water and hexanes and dried on high vacuum yielding the title compound as a white solid (696 mg, 75%). ES(+)-LRMS m/e calcd. for C48H45F4N7O10 (M+H)+ 956, obsd 956.

Workup

  1. concentrationThe reaction was concentrated
  2. dry with materialdried from acetonitrile yielding a white solid that
  3. additionwas mixed with DMSO (13 mL) and water (12 mL)
  4. temperatureThis mixture was heated minimally
  5. filtrationfiltered and to the filtrate
  6. additionwas added TFA (0.25 mL)
  7. customresulting in a precipitate
  8. filtrationfiltered
  9. washwashed with water and hexanes
  10. customdried on high vacuum

Sources & evidence

ORD record
ord-f2ef8a99c1c5490bb0ac8a62f56ab6b3
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447035B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes