Tert-Butylamine → HCID 25239132, compound

HRID 555989Notes

Reaction equation

HRID 555989 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=O.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:10]([O:9][C:7](=[O:8])[NH:1][CH2:2][CH2:3][C:4](=[O:6])[NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 25239132HCID 25239132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOC-Beta-Ala-OH (25 g, 0.132 mol) is dissolved in DCM (500 ml) and then treated with EDC1 (30.4 g, 0.59 mol) followed by t-butylamine (16.7 ml, 0.159 mol) to give a pale orange solution. The reaction mixture is stirred at room temperature overnight and then partitioned between 20% citric acid (400 ml) and DCM (250 ml). The organic portion is separated and washed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml), dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. additiontreated with EDC1 (30.4 g, 0.59 mol)
  2. customto give a pale orange solution
  3. custompartitioned between 20% citric acid (400 ml) and DCM (250 ml)
  4. customThe organic portion is separated
  5. washwashed with water (400 ml), saturated NaHCO3 (400 ml), brine (400 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bb55408e5d34ace87849c8b3aa1ea81
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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