1,2-Dichloroethane → Boc-D-Ala-NH2

HRID 77122

反応式

HRID 77122 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

HCID 7015296Boc-D-Ala-NH2収率 23.02%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-09a01529d70343c09047cf86e627c1cc
出典データセット
uspto-grants-2014_09
特許番号
US08835470B2

関連ノート

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