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

HRID 571440노트

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HRID 571440 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 54341824Methyl Boc-glycylglycyl-L-phenylalaninate수율 93.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-aa99fb954c314011ad6fc93373dc5101
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024093B2

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