Hydrochloric Acid → HCID 90289965, compound

HRID 1471639Notes

Reaction equation

HRID 1471639 reaction equation
C(=O)([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C@H:11]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:12]([N:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH3:15])=[O:13])[CH:5]=1)C.[OH-].[K+].C([N:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:39]1[CH2:53]Br)(=O)C.Cl>C(O)C>[C:28]([O:27][C:25]([NH:24][C@H:11]([C:12]([N:14]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[CH3:15])=[O:13])[CH2:10][C:6]1[CH:5]=[C:4]([S:3][CH2:53][C:39]2[NH:38][C:46]3[C:41]([C:40]=2[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:9]=[CH:8][CH:7]=1)=[O:26])([CH3:30])([CH3:31])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10860687HCID 10860687, compoundHCID 90327362HCID 90327362, compound

Product 1

HCID 90289965HCID 90289965, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)—S-3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenyl ethanethioate (335 mg, 0.73 mmol) in ethanol (2 ml) was added potassium hydroxide (82 mg, 1.46 mmol). After 10 minutes, ethyl 2-(1-acetyl-2-(bromomethyl)-1H-indol-3-yl)acetate (I-4A, 272 mg, 0.8 mmol) was added. The reaction was stirred for 2 hours and then neutralized with 1N (aq) HCl then extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (1-5% MeOH/DCM) to provide the desired product (347 mg, 0.55 mmol), 75.3%. MS (m/z) 632 [M+H]+.

Workup

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude product was introduced to a silica gel loading column
  6. custompurified by column chromatography (1-5% MeOH/DCM)

Sources & evidence

ORD record
ord-61e6fcd839a34329b8f3ed35177341fd
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

Loading…