Triethylamine → Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(benzo[b]thien-3-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

HRID 1080545

반응식

HRID 1080545 반응식
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:12]([NH:14][C:15]([CH3:29])([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)=[O:13])[CH2:8]2.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:54][CH2:55][CH2:56][C:57]1[C:58]2[CH:65]=[CH:64][CH:63]=[CH:62][C:59]=2[S:60][CH:61]=1.CCN(CC)CC>CN(C=O)C>[S:60]1[CH:61]=[C:57]([CH2:56][CH2:55][NH:54][C:26](=[O:27])[C:15]([NH:14][C:12](=[O:13])[O:11][CH:2]2[CH:1]3[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]2[CH2:4]4)[CH2:8]3)([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:29])[C:58]2[CH:65]=[CH:64][CH:63]=[CH:62][C:59]1=2

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 209554Benzo(b)thiophene-3-ethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 148025032-adamantyloxycarbonyl-alpha-methyl-DL-tryptophan

생성물 1

HCID 86747493Tricyclo[3.3.1.13,7]dec-2-yl (+/-)-[2-[[2-(benzo[b]thien-3-yl)ethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 0.50 g (1.26 mmol) of 2-adamantyl-oxycarbonyl-α-methyl-DL-tryptophan and 0.18 g (1.33 mmol) of 1-hydroxybenzotriazole hydrate in 8 mL of anhydrous DMF (under a N2 atmosphere) was treated in one portion with 0.27 g (1.41 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture was stirred at room temperature for 2 hours, treated with 0.30 g (1.40 mmole) of 3-[2-aminoethyl)benzo [b]thiophene hydrochloride plus 0.25 mL (0.18 g, 1.79 mmol) of Et3N, and stirred for an additional 18 hours. The reaction mixture was partitioned between 100 mL of EtOAc and 150 mL of H2O. The layers were separated and the aqueous layer extracted with fresh EtOAc (3×75 mL). The combined organic layers were washed with 5% aqueous citric acid (3×150 mL), brine (1×150 mL), 5% aqueous NaHCO3 (3×150 mL), and brine again. The organic layer was dried (Na2SO4) and evaporated (vacuum) to an off-white foam. The residue was chromatographed (230-400 mesh SiO2 in a 21×300 mm column, eluted with 2% MeOH in CH2Cl2) to yield the purified product as a white foam, 0.40 g (57%); 1H NMR (CDCl3) δ1.47-1.92 (17H, m), 2.92 (2H, t, J 7 Hz), 3.25 (1H, d, J 15 Hz), 3.46-3.57 (3H, m), 4.79 (1H, br s), 5.14 (1H, br s), 6.27 (1H, m), 7.02 (2H, m), 7.11-7.86 (8H, m), 8.10 (1H, br s).

후처리

  1. stirringstirred for an additional 18 hours
  2. customThe reaction mixture was partitioned between 100 mL of EtOAc and 150 mL of H2O
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with fresh EtOAc (3×75 mL)
  5. washThe combined organic layers were washed with 5% aqueous citric acid (3×150 mL), brine (1×150 mL), 5% aqueous NaHCO3 (3×150 mL), and brine again
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated (vacuum) to an off-white foam
  8. customThe residue was chromatographed (230-400 mesh SiO2 in a 21×300 mm column
  9. washeluted with 2% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-5207e17a55d0462aa99cd3c2a01a1ec9
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580896

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