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Methanol → (S)-2-[4-[[3,5-difluoro-4-[(S)-1-methoxycarbonyl-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 methyl ester

HRID 63753
Notes
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Reaction equation

HRID 63753 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[C:42]([F:69])[C:43]=1[C:44](=[O:68])[NH:45][C@H:46]([C:65]([OH:67])=[O:66])[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([C:54]2[C:55](=[O:64])[N:56]([CH3:63])[C:57](=[O:62])[N:58]([CH3:61])[C:59]=2[CH3:60])=[CH:50][CH:49]=1)[CH2:5][NH:6][CH2:7][C:8]1[CH:38]=[C:37]([F:39])[C:11]([C:12]([NH:14][C@@H:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:27](=[O:36])[N:28]([CH3:35])[C:29](=[O:34])[N:30]([CH3:33])[C:31]=3[CH3:32])=[CH:22][CH:21]=2)[C:16](O)=[O:17])=[O:13])=[C:10]([F:40])[CH:9]=1.[CH3:70][OH:71].[CH3:72]C(=O)OCC>C(Cl)Cl>[CH3:70][O:71][C:16](=[O:17])[C@@H:15]([NH:14][C:12](=[O:13])[C:11]1[C:37]([F:39])=[CH:38][C:8]([CH2:7][NH:6][CH2:5][C:4]2[CH:3]=[C:2]([F:1])[C:43]([C:44](=[O:68])[NH:45][C@H:46]([C:65]([O:67][CH3:72])=[O:66])[CH2:47][C:48]3[CH:49]=[CH:50][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:52][CH:53]=3)=[C:42]([F:69])[CH:41]=2)=[CH:9][C:10]=1[F:40])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[C:27](=[O:36])[N:28]([CH3:35])[C:29](=[O:34])[N:30]([CH3:33])[C:31]=2[CH3:32])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 89720667HCID 89720667, compound

Product 1

HCID 89720945(S)-2-[4-[[3,5-difluoro-4-[(S)-1-methoxycarbonyl-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 methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing (S)-2-[4-[[3,5-difluoro-4-[(S)-1-carboxy-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 (560 mg, 0.59 mmol) was added methanol (50 mL) and TMSCI (398 mg, 460 mL, 3.66 mmol) and the reaction was stirred overnight. Reaction was diluted with EA (10 mL), DCM (140 mL) and was washed with aqueous NaHCO3 solution (water:saturated solution 50 mL:50 mL, 10 mL brine) and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated yielding the title compound as a white solid and used directly as is. ES(+)-LRMS m/e calcd. for C50H49F4N7O10 (M+H)+ 984, obsd 984.

Workup

  1. customReaction
  2. washwas washed with aqueous NaHCO3 solution (water:saturated solution 50 mL:50 mL, 10 mL brine) and brine (100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-480e5d06b1d7486a9f70f80e9cb70cf2
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