Water → HCID 86725240, compound

HRID 576600Notes

Reaction equation

HRID 576600 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].C([O-])([O-])=O.[K+].[K+].Br[CH2:50][CH2:51][NH:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56].O>CN(C=O)C>[C:55]([O:54][C:53]([NH:52][CH2:51][CH2:50][N:35]1[CH2:34][C:33]2[C:37](=[CH:38][CH:39]=[C:31]([C:29]([NH:28][C@H:11]([B:9]3[O:8][CH:7]4[C:2]([CH3:1])([CH:3]5[CH2:40][CH:5]([CH2:6]4)[C:4]5([CH3:42])[CH3:41])[O:10]3)[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]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[O:30])[CH:32]=2)[CH2:36]1)=[O:59])([CH3:58])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86725241HCID 86725241, compound

Product 1

HCID 86725240HCID 86725240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (263 mg, 0.46 mmol) in DMF (5 mL) was added K2CO3 (252 mg, 1.84 mmol) and tert-butyl 2-bromoethylcarbamate (122 mg, 0.54 mmol). The resulting reaction was stirred at room temperature overnight. Water (15 mL) was added and the aqueous phase was extracted with EtOAc. The organic phase was washed with 1N HCl, brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (Hexane/EtOAc, 2:1 to 1:2). ESI-MS m/z 718.1 (MH)+.

Workup

  1. customThe resulting reaction
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe organic phase was washed with 1N HCl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (Hexane/EtOAc, 2:1 to 1:2)

Sources & evidence

ORD record
ord-69ace1147c4d40989743a2fb699ceb79
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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