1,2-Dichloroethane → Boc-D-Ala-NH2

HRID 77122

Reaction equation

HRID 77122 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:13])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:24]C=2C=1.N.O1CCOCC1.CN1CCOCC1>C(Cl)Cl>[NH2:24][C:10](=[O:11])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:13]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 79724-MethylmorpholineHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 637606BOC-D-alanine

Product 1

HCID 7015296Boc-D-Ala-NH2Yield 23.02%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-2-(tert-Butoxycarbonylamino)propanoic acid (1 g, 5.29 mmol), EDC (1.216 g, 6.34 mmol), and HOBt (0.971 g, 6.34 mmol) were dissolved in CH2Cl2 (5 mL). Ammonia (0.5 M) in dioxane (52.9 mL, 26.4 mmol) and 4-methylmorpholine (3.49 mL, 31.7 mmol) were added to the reaction mixture. After stirring for 1 h, the solvent was removed and ethyl acetate was added. This was washed with brine and saturated NaHCO3 solution. The organic layer was dried and concentrated to provide the product (R)-tert-butyl 1-amino-1-oxopropan-2-ylcarbamate (Int-X-A, 229 mg, 1.217 mmol, 23.02% yield); [M+Na]+=211.2; 1H NMR (400 MHz, methanol-d4) δ ppm 4.06 (1 H, q), 1.44 (9 H, s), 1.31 (3 H, d, J=7.04 Hz).

Workup

  1. customthe solvent was removed
  2. additionethyl acetate was added
  3. washThis was washed with brine and saturated NaHCO3 solution
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09a01529d70343c09047cf86e627c1cc
Source dataset
uspto-grants-2014_09
Patent number
US08835470B2

Linked notes

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