Hydrochloric Acid → HCID 86699102, compound

HRID 1424207Notes

Reaction equation

HRID 1424207 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:23]([O:25]C)=[O:24])[C:10]([CH3:22])([CH3:21])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Li+].[Br-].Cl>CC#N.O>[CH2:14]([O:13][C:11](=[O:12])[C:10]([CH3:22])([CH3:21])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:23]([OH:25])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 82050Lithium BromideHCID 86699122HCID 86699122, compound

Product 1

HCID 86699102HCID 86699102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-benzyl 1-methyl N-(tert-butoxycarbonyl)-3,3-dimethyl-L-aspartate (Preparation 45, 2 g, 5.47 mmol) in MeCN (30 mL) and water (0.6 mL) was added triethylamine (2.3 mL, 16.41 mmol) followed by LiBr (4.75 g, 54.73 mmol). The reaction mixture was stirred at room temperature for 3 days. The reaction was acidified with 1N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated in vacuo to afford the title compound that was used directly in the next step (1.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0b447a8681d40d1b81081b95e7c209d
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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