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 1669467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669467
[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

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe residue obtained by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-1cc84b56808c48efb271c37c8d7bef2e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989438B2

Notizen zur Reaktion

Wird geladen…