2-[34-Butan-2-yl-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetic acid → HCID 178453385, compound

HRID 589424Notes

Reaction equation

HRID 589424 reaction equation
[CH3:1][CH2:2][CH:3]([CH:5]1[NH:27][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[CH:20]2[NH:28][C:29]([CH:31]([CH:51]([CH:53]([OH:56])[CH2:54][OH:55])[CH3:52])[NH:32][C:33]([CH:35]3[N:39]([C:40]([CH:42]([CH2:46][C:47]([OH:49])=[O:48])[NH:43][C:44](=[O:45])[CH:13]([CH2:14][S:15]([C:17]4[NH:59][C:58]5[CH:60]=[C:61]([OH:64])[CH:62]=[CH:63][C:57]=5[C:18]=4[CH2:19]2)=[O:16])[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]1=[O:7])=[O:41])[CH2:38][CH:37]([OH:50])[CH2:36]3)=[O:34])=[O:30])[CH3:4].C(N(CC)CC)C.ClC(C([O-])=O)C(C)C.Cl.[C:81]([O:85][C:86]([NH:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][NH2:95])=[O:87])([CH3:84])([CH3:83])[CH3:82]>CN(C)C=O>[CH3:1][CH2:2][CH:3]([CH:5]1[NH:27][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[CH:20]2[NH:28][C:29]([CH:31]([CH:51]([CH:53]([OH:56])[CH2:54][OH:55])[CH3:52])[NH:32][C:33]([CH:35]3[N:39]([C:40]([CH:42]([CH2:46][C:47]([OH:49])=[O:48])[NH:43][C:44](=[O:45])[CH:13]([CH2:14][S:15]([C:17]4[NH:59][C:58]5[CH:60]=[C:61]([OH:64])[CH:62]=[CH:63][C:57]=5[C:18]=4[CH2:19]2)=[O:16])[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]1=[O:7])=[O:41])[CH2:38][CH:37]([OH:50])[CH2:36]3)=[O:34])=[O:30])[CH3:4].[C:81]([O:85][C:86]([N-:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][NH-:95])=[O:87])([CH3:84])([CH3:83])[CH3:82]

Participants

6

Reactant 4

HCID 22762-[34-Butan-2-yl-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetic acidHCID 8471Triethylamine2×HCID 3017638tert-Butyl (6-aminohexyl)carbamate monohydrochlorideHCID 19083669Chloroisobutylformate

Product 1

HCID 178453385HCID 178453385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

20 mg of dried β-amanitin (22 μmol) was dissolved in 0.3 ml of dried dimethylform-amide (DMF), and 0.005 ml of triethylamine was added. Under magnetic stirring, the reaction mixture was cooled to −18° C. (ice/NaCl) and after 10 min 0.164 ml of a mixture of 0.1 ml of chloroisobutylformate and 1.0 ml of DMF (110 μmol, 5 eq.) was added. The reaction was allowed to proceed for 20 min at −18° C. Fifty-five mg (220 μmol, 10 eq.) of t-butyloxy-carbonyl-hexamethylenediamine hydrochloride and 0.005 ml of triethylamine were dissolved in 0.3 ml of DMF, added to the reaction and stirred for 1 h at RT.

Workup

  1. additionadded to the reaction

Sources & evidence

ORD record
ord-70f0e626226740dbb216461eb91ac5f8
Source dataset
uspto-grants-2016_01
Patent number
US09233173B2

Reaction notes

Loading…