Acetic Acid → (16S,18R)-29-cyclohexyl-10,17-dimethyl-20-oxa-9-thia-1,8,10,13,17-pentaazahexacyclo[16.9.1.12,6.13,27.113,16.021,26]hentriaconta-2(31),3,5,21,23,25,27(29)-heptaen-7-one 9,9-dioxide

HRID 1669467노트

반응식

HRID 1669467 반응식
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:40]([NH:42][S:43]([N:46]([CH2:48]C(OC)OC)[CH3:47])(=[O:45])=[O:44])=[O:41])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C@H:16]([N:26]([CH3:39])[C@H:27]2[CH2:31][CH2:30][N:29]([C:32](OC(C)(C)C)=O)[CH2:28]2)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[BH3-]C#N.[Na+].CC(O)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O.CO>[CH:1]1([C:7]2[C:8]3[C:13]4=[CH:12][C:11](=[CH:10][CH:9]=3)[C:40](=[O:41])[NH:42][S:43](=[O:45])(=[O:44])[N:46]([CH3:47])[CH2:48][CH2:32][N:29]3[CH2:28][C@H:27]([CH2:31][CH2:30]3)[N:26]([CH3:39])[C@@H:16]3[CH2:15][N:14]4[C:21]=2[C:20]2[C:19]([O:18][CH2:17]3)=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 67344852tert-butyl (3S)-3-[{(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}amino)carbonyl]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl}(methyl)amino]pyrrolidine-1-carboxylate

생성물 1

HCID 86761385(16S,18R)-29-cyclohexyl-10,17-dimethyl-20-oxa-9-thia-1,8,10,13,17-pentaazahexacyclo[16.9.1.12,6.13,27.113,16.021,26]hentriaconta-2(31),3,5,21,23,25,27(29)-heptaen-7-one 9,9-dioxide

시약·촉매·용매 2

HCID 887Methanol용매HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A 0.05M solution of tert-butyl (3S)-3-[{(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)(methyl)amino]sulfonyl}amino)carbonyl]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl}(methyl)amino]pyrrolidine-1-carboxylate in DCM/TFA 3:1 was stirred at RT for 1.5 h. The residue obtained by evaporation was dissolved in MeOH, NEt3 (5 eq) was added, followed by NaCNBH3 (3 eq) and AcOH (10 eq) and the mixture was stirred for 4 h at RT.

후처리

  1. customThe residue obtained by evaporation

출처 및 근거

ORD 기록
ord-1cc84b56808c48efb271c37c8d7bef2e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989438B2

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