Dimethyl Sulfoxide → HCID 131733852, compound

HRID 708545Notes

Reaction equation

HRID 708545 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:21][CH2:22][OH:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H](C(O)=O)CC(O)=O.CCN(C(C)C)C(C)C.CS(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Si:1]([O:18][CH2:19][C@@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:21][CH:22]=[O:23])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5960L-Aspartic AcidHCID 81531DiisopropylethylamineHCID 69358153HCID 69358153, compound

Product 1

HCID 131733852HCID 131733852, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (S)-tert-butyl (1-((tert-butyldiphenylsilyl)oxy)-4-hydroxybutan-2-yl)carbamate (prepared according to the procedure described in WO2013124826 A1 using L-aspartic acid) (15.0 g, 33.8 mmol) and DIPEA (29.5 mL, 169 mmol) in DCM (50 mL) at 0° C. was added a slurry of DMSO (7.20 mL, 101 mmol) and sulfurtrioxide pyridine complex (16.14 g, 101 mmol) in DCM (50 mL). After stirring at rt for 1.5 h, the mixture was diluted with saturated NaHCO3 (aq) and the layers were separated. The aqueous layer was extracted with DCM and the combined organic portions were dried over Na2SO4 and concentrated in vacuo to afford the title compound (16.9 g, assumed quantitative) as a ight brown oil. It was used as such without further purification. LCMS: Rt=1.20 min, m/z=442.2 (M+1) Method 2m_acidic.

Workup

  1. customat 0° C.
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialthe combined organic portions were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea2452124ee84e5a8ae11ac464134905
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…