1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59437171, 화합물

HRID 75142

반응식

HRID 75142 반응식
[C:1]12([CH2:11][NH2:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:13][C@@H:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15](O)=[O:16].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]12([CH2:11][NH:12][C:15](=[O:16])[C@@H:14]([OH:13])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 439616(S)-mandelic acid

생성물 1

HCID 59437171HCID 59437171, 화합물수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1-adamantyl)methylamine (100 mg, 0.61 mmol), (S)-2-hydroxy-2-phenylacetic acid (92 mg, 0.61 mmol), EDCI (239 mg, 1.22 mmol) and HOBt (164 mg, 1.22 mmol) in CH2Cl2 (15 mL) was added DIEA (391 mg, 3.03 mmol) and the resulting mixture was stirred overnight. The solution was concentrated under vacuum to give the crude product, which was purified by preparative TLC to afford (S)—N-((1-adamantyl)methyl)-2-hydroxy-2-phenylacetamide (85 mg, 47%). 1H NMR (CDCl3, 400 MHz): δ=1.34-1.91 (m, 15H), 2.86 (q, 1H), 3.02 (q, 1H), 5.04 (s, 1H), 5.93 (s, 1H), 7.25-7.43 (m, 5H).

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

출처 및 근거

ORD 기록
ord-48e2a0bedcdc43189f5c344b9464dd66
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835426B2

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