tert-butyl 3-((2R)-2-(3-((S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate → tert-butyl 3-((2R)-2-(3-((S)-2-amino-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate

HRID 2208578Notes

Reaction equation

HRID 2208578 reaction equation
C(OC([NH:11][C@@H:12]([CH2:59][NH:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:52]=[CH:53][C:54]=1[CH2:55][N:56]([CH3:58])[CH3:57])[C:19]([NH:21][C@H:22]([B:39]1[O:47][CH:46]2[C:41]([CH3:51])([CH:42]3[CH2:48][CH:44]([CH2:45]2)[C:43]3([CH3:50])[CH3:49])[O:40]1)[CH2:23][C:24]1[C:25]([O:37][CH3:38])=[C:26]([CH:34]=[CH:35][CH:36]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:20])=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]([CH2:59][NH:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:52]=[CH:53][C:54]=1[CH2:55][N:56]([CH3:57])[CH3:58])[C:19]([NH:21][C@H:22]([B:39]1[O:47][CH:46]2[C:41]([CH3:51])([CH:42]3[CH2:48][CH:44]([CH2:45]2)[C:43]3([CH3:50])[CH3:49])[O:40]1)[CH2:23][C:24]1[C:25]([O:37][CH3:38])=[C:26]([CH:34]=[CH:35][CH:36]=1)[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[O:20])=[O:14]

Participants

4

Reactant 1

HCID 86725254tert-butyl 3-((2R)-2-(3-((S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate

Product 1

HCID 86725256tert-butyl 3-((2R)-2-(3-((S)-2-amino-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoateYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To tert-butyl 3-((2R)-2-(3-((S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanamido)-4-((dimethylamino)methyl)benzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (130 mg) in MeOH (20 mL was added 10% Pd/C (20 mg). The reaction mixture was stirred under H2 balloon for 6 hr. The catalyst was removed by filtration and MeOH removed under reduced pressure to afford the product (90 mg) which was carried on to the next step.

Workup

  1. customThe catalyst was removed by filtration and MeOH
  2. customremoved under reduced pressure

Sources & evidence

ORD record
ord-d6e640c392db48ba946036bd5c2f0d45
Source dataset
uspto-grants-2016_06
Patent number
US09376454B2

Reaction notes

Loading…