Methanol → HCID 49800412, compound

HRID 391935Notes

Reaction equation

HRID 391935 reaction equation
C[O:2][C:3](=[O:60])[C@@H:4]([NH:20][C:21]([C@@H:23]1[CH2:32][C:31]2[CH:30]=[C:29]3[O:33][CH2:34][C@H:35]([C:37]4[CH:42]=[CH:41][C:40]([O:43][C:44]5[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[CH:45]=5)=[CH:39][CH:38]=4)[O:36][C:28]3=[CH:27][C:26]=2[CH2:25][N:24]1[C:51]([C:53]1[N:54]=[C:55]([CH3:59])[O:56][C:57]=1[CH3:58])=[O:52])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[C:13]=2[CH3:19])=[CH:8][CH:7]=1.CO.[Li+].[OH-]>C1COCC1>[Cl:50][C:46]1[CH:45]=[C:44]([CH:49]=[CH:48][CH:47]=1)[O:43][C:40]1[CH:39]=[CH:38][C:37]([C@H:35]2[CH2:34][O:33][C:29]3=[CH:30][C:31]4[CH2:32][C@@H:23]([C:21]([NH:20][C@@H:4]([CH2:5][C:6]5[CH:11]=[CH:10][C:9]([C:12]6[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[C:13]=6[CH3:19])=[CH:8][CH:7]=5)[C:3]([OH:60])=[O:2])=[O:22])[N:24]([C:51]([C:53]5[N:54]=[C:55]([CH3:59])[O:56][C:57]=5[CH3:58])=[O:52])[CH2:25][C:26]=4[CH:27]=[C:28]3[O:36]2)=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 66719731HCID 66719731, compound

Product 1

HCID 49800412HCID 49800412, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-{[(3S,8S)-3-[4-(3-Chloro-phenoxy)-phenyl]-7-(2,5-dimethyl-oxazole-4-carbonyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yl)-phenyl]-propionic acid methyl ester (0.020 g) dissolved in THF (0.3 mL) and MeOH (0.3 mL) and 0.3 mL of 2.0 N LiOH was added at 0° C. and stirred at that temperature for 30 minutes. The pH was adjusted to 6-7, and the mixture was extracted with EtOAc, dried with (Na2SO4), and evaporated and dried under vacuum to get the title compound (0.015 g). LCMS (m/z): 814.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialdried with (Na2SO4)
  3. customevaporated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-375e59916df64adaacbb5e2082d80f9c
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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