Hydrochloric Acid → HCID 85433067, compound

HRID 2298229Notes

Reaction equation

HRID 2298229 reaction equation
[NH2:1][C@@H:2]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[CH:20]1[C:28]2[C:27]3[CH2:29][CH2:30][CH2:31][CH2:32][C:26]=3[O:25][C:24]=2[CH:23]=[C:22]([S:33](Cl)(=[O:35])=[O:34])[CH:21]=1.Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:4][CH:3]([CH3:5])[CH:2]([NH:1][S:33]([C:22]1[CH:21]=[CH:20][C:28]2[C:27]3[CH2:29][CH2:30][CH2:31][CH2:32][C:26]=3[O:25][C:24]=2[CH:23]=1)(=[O:34])=[O:35])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6931638tert-butyl D-valinateHCID 11219458HCID 11219458, compound

Product 1

HCID 85433067HCID 85433067, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (D)-valine, teri-butyl ester (0.13 g, 0.74 mmol) and triethylamine (0.075 g, 0.74 mmol) in tetrahydrofuran/water (5 mL, 1:1) was added in one portion at room temperature 6,7,8,9-tetrahydro-dibenzofuran-3-sulfonyl chloride (0.20 g, 0.74 mmol). The reaction mixture was stirred at room temperature for 14 hours, followed by the addition of aqueous HCl (1 M, 5 mL) and ethyl acetate (10 mL). The organic phase was separated and washed with brine, dried (MgSO4), and concentrated to dryness to give the title compound as a white solid (0.24 g, 80%).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-523dd20388b44fc2bc4fa08a0163cfe1
Source dataset
uspto-grants-2002_12
Patent number
US06492422B2

Reaction notes

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