HCID 86722939, compound → HCID 86722938, compound

HRID 1404329Notes

Reaction equation

HRID 1404329 reaction equation
[C:1]([O:5][C:6](=[O:52])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([NH:28][C:29](=[O:49])[CH2:30][CH:31]2[CH2:36][CH2:35][CH:34]([CH2:37][NH:38]C(OCC3C=CC=CC=3)=O)[CH2:33][CH2:32]2)[B:15]2[O:23][CH:22]3[C:17]([CH3:27])([CH:18]4[CH2:24][CH:20]([CH2:21]3)[C:19]4([CH3:26])[CH3:25])[O:16]2)[C:8]=1[O:50][CH3:51])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:52])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([NH:28][C:29](=[O:49])[CH2:30][CH:31]2[CH2:32][CH2:33][CH:34]([CH2:37][NH2:38])[CH2:35][CH2:36]2)[B:15]2[O:23][CH:22]3[C:17]([CH3:27])([CH:18]4[CH2:24][CH:20]([CH2:21]3)[C:19]4([CH3:25])[CH3:26])[O:16]2)[C:8]=1[O:50][CH3:51])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86722939HCID 86722939, compound

Product 1

HCID 86722938HCID 86722938, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[2-{2-[4-(Benzyloxycarbonylamino-methyl)-cyclohexyl]-acetylamino}-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-2-methoxy-benzoic acid tert-butyl ester (1.56 g, 2.18 mmol) in MeOH (22 mL) was purged with Argon for 5 minutes. Palladium on carbon (10%, 0.153 g) was added, flask evacuated, and the reaction stirred under hydrogen atmosphere for 6.5 hr. The reaction was filtered through a Celite-plugged filter frit, washed with MeOH and DCM, and concentrated to provide 1.29 g of crude product that was carried to the next step without purification. ESI-MS m/z 583 (MH)+.

Workup

  1. customflask evacuated
  2. filtrationThe reaction was filtered through a Celite-plugged filter frit
  3. washwashed with MeOH and DCM
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5f288250fa7344e58f19238051aa516e
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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