Potassium Carbonate → {N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid tert-butyl ester

HRID 507303Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:26]([O:30][C:31](=[O:34])[CH2:32]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[C:26]([O:30][C:31](=[O:34])[CH2:32][N:11]([C@@H:12]([C:13](=[O:14])[NH2:15])[CH2:16][CH:17]([CH3:19])[CH3:18])[S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide (3.00 g, 9.87 mmol) was dissolved in DMF (50 mL). To the solution was added potassium carbonate (6.0 g, 39 mmol) and bromoacetic acid tert-butyl ester (6.0 mL, 39 mmol). The solution was heated to 70° C. for 3 h. The reaction was quenched with EtOAc and saturated NaHCO3. The organic layer was washed with brine, dried over MgSO4, and concentrated. The crude oil was further purified on a Biotage 40M (loaded in CH2Cl2, eluted in 30% EtOAc/hexanes) to afford a white powder (1.2 g, 35%). MS (ESI), (M+H)+ 446.3; 1H NMR (CDCl3) δ 7.76 (d, 2H, J=8.0), 7.52 (d, 2H, J=8.0), 6.61 (br s, 1H) 5.45 (s, 1H), 4.15-4.18 (m, 1H), 3.09-3.24 (m, 2H), 2.50-2.58 (m, 4H), 2.31-2.39 (m, 2H), 1.92-1.99 (m, 1H), 1.15-1.59 (m, 8H), 1.00-1.04 (m, 7H), 0.71-0.74 (m, 6H).

Workup

customThe reaction was quenched with EtOAc and saturated NaHCO3
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude oil was further purified on a Biotage 40M (loaded in CH2Cl2, eluted in 30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a6e288e44f13429880b7f1f2eadaef70
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786122B2

Reaction notes

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