Water → HCID 86725262, compound

HRID 1478858Notes

Reaction equation

HRID 1478858 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][C:43]=1[OH:44])[C:8]([NH:10][C@H:11]([B:28]1[O:36][CH:35]2[C:30]([CH3:40])([CH:31]3[CH2:37][CH:33]([CH2:34]2)[C:32]3([CH3:39])[CH3:38])[O:29]1)[CH2:12][C:13]1[C:14]([O:26][CH3:27])=[C:15]([CH:23]=[CH:24][CH:25]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:9])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:52][CH2:53][NH:54]C(=O)OC(C)(C)C.O>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][C:43]=1[O:44][CH2:52][CH2:53][NH2:54])[C:8]([NH:10][C@H:11]([B:28]1[O:36][CH:35]2[C:30]([CH3:40])([CH:31]3[CH2:37][CH:33]([CH2:34]2)[C:32]3([CH3:39])[CH3:38])[O:29]1)[CH2:12][C:13]1[C:14]([O:26][CH3:27])=[C:15]([CH:23]=[CH:24][CH:25]=1)[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86725263HCID 86725263, compound

Product 1

HCID 86725262HCID 86725262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To tert-butyl 3-((2R)-2-(3-acetoxy-4-hydroxybenzamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (100 mg from step 1) in DMF (3 mL) was added K2CO3 (100 mg) followed by tert-butyl 2-bromoethylcarbamate (100 mg). The resulting reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extracted with EtOAc three times. The combined organic phases were dried and concentrated to afford the product which was carried on to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc three times
  3. customThe combined organic phases were dried
  4. concentrationconcentrated
  5. customto afford the product which
  6. customwas carried on to the next step without further purification

Sources & evidence

ORD record
ord-7c7088084aa241edb34c04a8586618ac
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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