Dichloromethane → HCID 86649435, compound

HRID 1261710Notes

Reaction equation

HRID 1261710 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14](OCC)=[O:15])=[C:10]([OH:19])[C:9]3[CH2:20][O:21][CH2:22][C:8]2=3)=[CH:4][CH:3]=1.C([NH:29][CH2:30][C:31]([OH:33])=[O:32])(C)(C)C.C(Cl)Cl>COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:29][CH2:30][C:31]([O:33][CH2:24][CH2:2][CH2:3][CH3:4])=[O:32])=[O:15])=[C:10]([OH:19])[C:9]3[CH2:20][O:21][CH2:22][C:8]2=3)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 414246N-tert-ButylglycineHCID 59637183HCID 59637183, compound

Product 1

HCID 86649435HCID 86649435, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the ester from Step C (563 mg, 1.43 mmol) in 1,2-dimethoxyethane (12 mL) was added tert-butyl glycine (0.390 mL, 2.86 mmol). The mixture was heated in the microwave at 120° C. for 1.5 h. The mixture was concentrated in vacuo to give a yellow oil which was taken up in the minimum amount of CH2Cl2 and chromatographed on a Biotage 40S+ column with a 10, 20, 30, EtOAc/hexanes gradient elution to give compound, 28-4, as a white solid, 494 mg: 1H NMR (500 MHz, CDCl3): δ 1.49 (s, 9 H), 4.09 (d, 2 H, J=5.2 Hz), 4.91 (t, 2 H, J=3.2 Hz), 5.01 (s, 2 H), 5.05 (t, 2 H, J=3.2 Hz), 7.09 (d, 2 H, 8.3 Hz), 7.46 (d, 2 H, J=8.2 Hz), 10.44 (m, 1 H); HPLC/MS: 1.28 min, 480.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a yellow oil which
  3. customchromatographed on a Biotage 40S+ column with a 10, 20, 30, EtOAc/hexanes gradient elution
  4. customto give compound, 28-4
  5. custom1.28 min, 480.0 (M+H)+

Sources & evidence

ORD record
ord-888497be97a2405d958d28666f178f16
Source dataset
uspto-grants-2013_06
Patent number
US08471024B2

Reaction notes

Loading…