1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl Boc-glycylglycyl-L-phenylalaninate

HRID 571440ノート

反応式

HRID 571440 の反応式
[C:1]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:38][O:39][C:40](=[O:50])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH2:42]>C1COCC1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:38][O:39][C:40](=[O:50])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH:42][C:14](=[O:16])[CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 736234L-Phenylalanine, methyl ester

生成物 1

HCID 54341824Methyl Boc-glycylglycyl-L-phenylalaninate収率 93.2%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To N-Boc-glycylglycine (696 mg, 3.00 mmol, 1.00 equiv) in THF (10.0 mL) at 0° C. was added EDCI (1.15 g, 6.00 mmol, 2.00 equiv), HOBt (810 mg, 6.00 mmol, 2.00 equiv), n,n-diisopropylethyl amine (1.56 mL, 9.00 mmol, 3.00 equiv) and 4-(Dimethylamino)pyridine (36 mg, 0.030 mmol, 0.10 equiv) and L-phenylalanine methyl ester (647 mg, 3.00 mmol, 1.00 equiv). The reaction mixture was stirred for 1 hr at 0° C. and stirred for 12 h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and dried (Na2SO4). The filtrate is concentrated in vacuo and the residue is purified by chromatography on silica gel eluting with DCM/MeOH 10:1 (v/v) to afford 1.10 g of the title compound as a colorless oil (93% yield).

後処理

  1. stirringstirred for 12 h at room temperature
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by chromatography on silica gel eluting with DCM/MeOH 10:1 (v/v)

出典と根拠

ORDレコード
ord-aa99fb954c314011ad6fc93373dc5101
出典データセット
uspto-grants-2015_05
特許番号
US09024093B2

反応ノート

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