tert-Butyl bromoacetate → HCID 117732278, compound

HRID 1772649Notes

Reaction equation

HRID 1772649 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]3[CH:20]=[C:21]([CH2:23][O:24][C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=[C:18]3[C:17]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[N:16][CH:15]=2)[CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.Br[CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53]>C1COCC1>[O:38]1[CH2:39][CH2:40][N:35]([C:17]2[C:18]3[N:19]([CH:20]=[C:21]([CH2:23][O:24][C:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[N:26]=4)[N:22]=3)[C:14]([CH:11]3[CH2:10][CH2:9][N:8]([CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:13][CH2:12]3)=[CH:15][N:16]=2)[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 86345566HCID 86345566, compound

Product 1

HCID 117732278HCID 117732278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 111 (50 mg, 0.06 mmol, Example 26), DIEA (53 μL, 0.38 mmol) and tert-butyl bromoacetate (12 μL, 0.07 mmol) in THF (1 mL) was heated at 120° C. in a microwave for 10 min. The reaction mixture was allowed to cool to rt and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:1-1:0 EtOAc/hexanes) to obtain compound 27a. Mass Spectrum (LCMS, ESI pos.) Calcd. For C31H38N6O4: 559.3 (M+H). Found 559.3.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas purified by flash column chromatography on silica gel (0:1-1:0 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a42942763074462c9aece092f93f6b1c
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…