Carbamate → 2-(4-{2-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenylcarbamoyloxymethyl}-phenoxycarbonylamino)-pentanedioic acid diallyl ester

HRID 33992

반응식

HRID 33992 반응식
C(=O)([O-])N.[CH2:5]([O:8][C:9](=[O:31])[CH:10]([NH:19][C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=1)=[O:21])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH:6]=[CH2:7].C(N(CC)CC)C.[C:39]([SiH2:43][O:44][C:45]([CH3:67])([CH3:66])[CH:46]1[CH2:50][CH2:49][CH2:48][N:47]1[C:51]([C:53]1[CH:58]=[C:57]([O:59][CH3:60])[C:56]([O:61][CH3:62])=[CH:55][C:54]=1[N:63]=[C:64]=[O:65])=[O:52])([CH3:42])([CH3:41])[CH3:40].NC1C=C(OC)C(OC)=CC=1C(N1CCCC1C(C)(C)O[SiH2]C(C)(C)C)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:5]([O:8][C:9](=[O:31])[CH:10]([NH:19][C:20]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][O:30][C:64](=[O:65])[NH:63][C:54]2[CH:55]=[C:56]([O:61][CH3:62])[C:57]([O:59][CH3:60])=[CH:58][C:53]=2[C:51]([N:47]2[CH2:48][CH2:49][CH2:50][CH:46]2[C:45]([CH3:67])([CH3:66])[O:44][SiH2:43][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:52])=[CH:27][CH:28]=1)=[O:21])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH:6]=[CH2:7]

참가 물질

10

반응물 6

HCID 276CarbamateHCID 8471Triethylamine2회HCID 94429TriphosgeneHCID 690331942-(4-Hydroxymethyl-phenoxycarbonylamino)-pentanedioic acid diallyl esterHCID 131727078[2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-(2-isocyanato-4,5-dimethoxy-phenyl)-methanoneHCID 131727079(2-Amino-4,5-dimethoxy-phenyl)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-methanone

생성물 1

HCID 1317270812-(4-{2-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carbonyl]-4,5-dimethoxy-phenylcarbamoyloxymethyl}-phenoxycarbonylamino)-pentanedioic acid diallyl ester

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of the carbamate progroup 42 (1.48 g, 3.92 mmol) and triethylamine (0.45 g, 0.6 mL, 4.3 mmol) in anhydrous CH2Cl2 (30 mL) was added to a solution of the isocyanate 7 prepared from the amine 5 (1.54 g, 3.92 mmol), triphosgene (0.42 g, 1.4 mmol) and triethylamine (0.535 g, 0.74 mL, 5.3 mmol) in anhydrous toluene (50 mL). The reaction was complete in 4 h. The product was obtained (flash column chromatography 40% EtOAc/60% n-hexane) as a colourless oil (1.76 g, 56). 1H NMR (CDCl3) δ 9.22 (bs, 1H), 7.87 (s, 1H), 7.40 (d, J=10 Hz, 2H), 7.13 (d, J=7.5 Hz, 2H), 6.83 (s, 1H), 5.93 (m, 2H), 5.74 (d, J=8.3 Hz, 1H), 5.30 (m, 4H), 5.17 (d, J=12.5 Hz, 1H), 5.15 (d, J=12.5 Hz, 1H) 4.68 (d, J=5 Hz, 2H) 4.61 (d, J=5 Hz, 1H), 4.48 (m, 1H), 4.35 (m, 1H), 3.95 (s, 3H), 3.82 (s, 3H), 3.65 (m, 1H), 3.50 (m, 2H), 2.55 (m, 2H), 2.30 (m, 1H), 2.1 (m, 3H), 1.95 (m, 1H), 1.8 (m, 1H), 0.9 (s, 9H), 0.04 (s, 6H). IR (neat) 3338, 2953, 2857, 1735, 1615, 1597, 1522 cm−1.

출처 및 근거

ORD 기록
ord-85205595cf7c4285955a4dd8b71a252e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429658B2

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