Diisopropylethylamine → HCID 58017454, compound

HRID 1879233Notes

Reaction equation

HRID 1879233 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)[C@@H:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.C[CH2:37][N:38](C(C)C)[CH:39](C)C>C(Cl)Cl.CNC.C1COCC1>[CH3:37][N:38]([CH3:39])[CH2:30][CH2:29][CH2:28][N:12]([S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[C@@H:13]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 58017461HCID 58017461, compound

Product 1

HCID 58017454HCID 58017454, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 674DimethylamineSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl N-[(3-methoxyphenyl)sulfonyl]-3-methyl-N-{3-[(methylsulfonyl)oxy]propyl}-D-valinate (2.00 g, 3.79 mmol) in DCM (15 mL), dimethylamine in THF (2M, 9.5 mmol, 19.0 mmol) and DIPEA (1.99 mL, 11.4 mmol) are added, and the reaction mixture is allowed to stir at rt for 18 h. Additional 3.0 mL of dimethylamine in THF (2M) is added to the reaction mixture and is allowed to stir for additional 3 d. The reaction was approximately 50% complete. The reaction mixture is concentrated in vacuo and is purified by silica gel chromatography eluting with a gradient of 5-100% EtOAc/heptane to obtain the desired intermediate (500 mg, 28% yield). Mass spectrum (477.5; M+1).

Workup

  1. stirringto stir for additional 3 d
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customis purified by silica gel chromatography
  4. washeluting with a gradient of 5-100% EtOAc/heptane

Sources & evidence

ORD record
ord-6d71e948e99b4058bc7cc6498411624f
Source dataset
uspto-grants-2012_11
Patent number
US08314148B2

Reaction notes

Loading…