Hydrochloric Acid → HCID 53252317, compound

HRID 1039029Notes

Reaction equation

HRID 1039029 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:29][CH3:30])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=2)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:29][CH3:30])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67236696HCID 67236696, compound

Product 1

HCID 53252317HCID 53252317, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 200 mL round bottom flask was charged with (S)-methyl 2-(3-(2-(tert-butoxycarbonylamino)butanamido)propyl)-1H-indole-5-carboxylate (1.67 g, 4.00 mmol), tetrahydrofuran (20 mL), and methanol (5.3 mL). 3N Sodium hydroxide (4.0 mL, 12.0 mmol) was added and the resulting mixture stirred and heated to 50° C. for 8 h. The resulting mixture was then cooled to room temperature and acidified with 1N hydrochloric acid. The resulting mixture was extracted two times with ethyl acetate (400 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield (S)-2-(3-(2-(tert-butoxycarbonylamino)butanamido)propyl)-1H-indole-5-carboxylic acid. 1H NMR (300 MHz, CD3OD) δ 8.20 (s, 1H), 7.75 (d, J=7.0 Hz, 1H), 7.32 (d, J=8.6 Hz, 1H), 6.31 (s, 1H), 3.94-4.10 (m, 1H), 3.22-3.34 (m, 2H), 2.80-2.85 (m, 2H), 1.61-2.08 (m, 4H), 1.46 (s, 9H), and 0.93-1.03 (m, 3H); MS (ES+) 403 (M+1).

Workup

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. extractionThe resulting mixture was extracted two times with ethyl acetate (400 mL)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61c54f875f894ceab1efc8428f2c4bb3
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

Loading…