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 1669467Notes

Reaction equation

HRID 1669467 reaction equation
[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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

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.

Workup

  1. customThe residue obtained by evaporation

Sources & evidence

ORD record
ord-1cc84b56808c48efb271c37c8d7bef2e
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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