Methanol → 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one

HRID 1818453노트

반응식

HRID 1818453 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[C:12]([O:14]C(=O)C3C=CC=CC=3)([CH3:13])[CH:11]([O:23]C(=O)C3C=CC=CC=3)[CH:10]([CH2:32][O:33]C(=O)C3C=CC=CC=3)[O:9]2)[C:4](=[O:42])[N:3]=1.C(OC(N[C@H](C(O)=O)C(C)C)=O)(C)(C)C.Cl.CN(C)CCCN=C=NCC.CO>ClCCl.CN(C)C1C=CN=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]2[C:12]([OH:14])([CH3:13])[CH:11]([OH:23])[CH:10]([CH2:32][OH:33])[O:9]2)[C:4](=[O:42])[N:3]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 83693Boc-L-Valine2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 671753714-amino-1-(3,4-dibenzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydrofuran-2-yl)-1H-pyrimidin-2-one

생성물 1

HCID 138710334-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

A solution of compound (5) (58 g, 0.1053 mol) in dichloromethane (500 ml) was stirred at 25° C. under argon atmosphere. N-(tert-butoxycarbonyl)-L-valine (29.7 g, 0.1367 mol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (26.2 g, 0.1367 mol) and 4-(dimethylamino)pyridine (1.3 g, 0.0106 mol) were added and the reaction mixture was stirred at 25° C. and monitored by HPLC (method #2). After 4 hours, HPLC showed 7.9% of starting material. N-(tert-butoxycarbonyl)-L-valine (4.57 g, 0.0210 mol) and 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (4.03 g, 0.0210 mol) were added and stirring was continued at 25° C. for an additional period of 2 hours, after which, HPLC detected 0.7% of starting material. Methanol (60 ml) was added to the reaction mixture and solvents were evaporated under reduced pressure (temperature kept below 40° C.) to give compound (6) as thick oil. This material (93% pure by HPLC/AUC) was used as is for the subsequent reaction.

후처리

  1. stirringstirring
  2. waitwas continued at 25° C. for an additional period of 2 hours
  3. customwere evaporated under reduced pressure (temperature kept below 40° C.)

출처 및 근거

ORD 기록
ord-3b32147a98d440aca67f72115588ef4e
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598373B2

반응 노트

불러오는 중…