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 576615Notes

Reaction equation

HRID 576615 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-3d669147a1224c4dbdecdbad43a60e7c
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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