Hydrochloric Acid → (S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

HRID 339235Notes

Reaction equation

HRID 339235 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:48])[C@@H:9]([CH3:47])[C:10]([NH:12][C@@H:13]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:14]([N:16]1[C@H:25]([C:26](=[O:38])[NH:27][C@H:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][CH2:29]2)[CH2:24][C:23]2[C:18](=[CH:19][C:20]([C:39]([O:41]C)=[O:40])=[CH:21][CH:22]=2)[CH2:17]1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CCOC(C)=O.Cl>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]([CH3:48])[C@@H:9]([CH3:47])[C:10]([NH:12][C@@H:13]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:14]([N:16]1[C@H:25]([C:26](=[O:38])[NH:27][C@H:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][CH2:29]2)[CH2:24][C:23]2[C:18](=[CH:19][C:20]([C:39]([OH:41])=[O:40])=[CH:21][CH:22]=2)[CH2:17]1)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86705869(S)-Methyl 2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

Product 1

HCID 86705870(S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acidYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (1.34 g, 2.02 mmol) in THF (13.5 mL) and MeOH (6.7 mL) was added NaOH(aq.) (3N, 3.4 mL, 10.1 mmol). After 3 h, the reaction mixture was poured into a sep funnel containing EtOAc and 1N HCl. The aqueous layer was extracted with EtOAc (3×), and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (1.25 g, 1.93 mmol, 95%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 649.3 (M+H)+.

Workup

  1. additionthe reaction mixture was poured into a sep funnel
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e707610a1c31428eb7d3f0e644dd0430
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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