Water → HCID 86725242, compound

HRID 576602Notes

Reaction equation

HRID 576602 reaction equation
[CH3:1][C:2]12[O:10][B:9]([C@@H:11]([NH:28][C:29]([C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[CH2:36][NH:35][CH2:34]4)=[O:30])[CH2:12][C:13]3[C:14]([O:26][CH3:27])=[C:15]([CH:23]=[CH:24][CH:25]=3)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[O:8][CH:7]1[CH2:6][CH:5]1[CH2:40][CH:3]2[C:4]1([CH3:42])[CH3:41].[CH:43](=O)[C:44]1[CH:49]=[CH:48][CH:47]=[N:46][CH:45]=1.O>ClCCCl>[CH3:27][O:26][C:14]1[C:13]([CH2:12][C@H:11]([NH:28][C:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[CH2:36][N:35]([CH2:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)[CH2:34]3)=[O:30])[B:9]2[O:8][CH:7]3[C:2]([CH3:1])([CH:3]4[CH2:40][CH:5]([CH2:6]3)[C:4]4([CH3:42])[CH3:41])[O:10]2)=[CH:25][CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 86725241HCID 86725241, compound

Product 1

HCID 86725242HCID 86725242, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To tert-butyl 3-((2R)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-2-(isoindoline-5-carboxamido)ethyl)-2-methoxybenzoate from Example 9 step 2 (240 mg, 0.42 mmol) in 1,2-dichloroethane (5 mL) was added nicotinaldehyde (90 mg, 0.84 mmol) and Na(OAc)3BH4 (211 mg, 1 mmol). The reaction mixture was stirred at room temperature for 6 hr. Water (10 mL) was added at 0° C. and the aqueous phase was extracted with EtOAc. The organic phase was washed brine, dried over Na2SO4 and concentrated in vacuo. The crude product was carried to the next step without further purification. ESI-MS m/z 666.1 (MH)+.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washThe organic phase was washed brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was carried to the next step without further purification

Sources & evidence

ORD record
ord-7d47f21b7dc6415a9e291db053be40df
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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