N,N-Dimethylglycine → HCID 131729368, compound

HRID 420281Notes

Reaction equation

HRID 420281 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:32].[CH3:33][N:34]1[CH2:39]C[O:37][CH2:36][CH2:35]1.CN(C)CC(O)=O>CN(C=O)C.CCOC(C)=O>[C:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:12]1[C@@H:11]2[C@H:15]([C@H:7]([CH2:6][C:5]3[CH:30]=[CH:31][C:2]([NH:1][C:36](=[O:37])[CH2:35][N:34]([CH3:39])[CH3:33])=[C:3]([F:32])[CH:4]=3)[CH2:8][S:9](=[O:28])(=[O:29])[CH2:10]2)[O:14][C:13]1=[O:16])([CH3:26])([CH3:27])[CH3:25]

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 79724-MethylmorpholineHCID 66649435HCID 66649435, compound

Product 1

HCID 131729368HCID 131729368, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3aR*,7S*,7aS*)-7-(4-amino-3-fluoro-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1oxa-5lambda*6*-thia-3-aza-inden-2-one (example 1j), 1.06 g, 2.3 mmol), N-methylmorpholine (0.507 mL, 4.6 mmol), N,N-dimethylglycine (0.356 g, 3.45 mmol) and propylphosphoric acid anhydride (50% in DMF, 2.68 mL, 4.6 mmol) was stirred in DMF (9.2 mL) at 25° C. for 19 h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3 solution, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to leave the title compound as a colorless, amorphous powder: TLC (toluene-ETA 85:15) Rf=0.36; HPLC RtA=1.84 min; ESIMS [M+H]+=546; 1H NMR (600 MHz, DMSO-d6): δ 9.46 (s, 1H), 7.85 (t, 1H), 7.39 (s, 1H), 7.32 (d, 1H), 7.28 (t, 1H), 7.17-7.11 (m, 2H), 7.0 (d, 1H), 4.42 (d, 1H), 4.23 (d, 1H), 4.16 (t, 1H), 3.74-3.65 (m, 2H), 3.45 (t, 1H), 3.08 (m, 3H), 3.01 (m, 1H), 2.93 (m, 1H), 2.58 (m, 1H), 2.52 (m, 1H), 2.30 (s, 6H), 1.25 (s, 9H).

Workup

  1. washwashed with saturated NaHCO3 solution, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-dacece7ef1644207b0fe8e8bcb4b720b
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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