Silane, tris(1-methylethyl)- → HCID 53476668, compound

HRID 2204964Notes

Reaction equation

HRID 2204964 reaction equation
[C:1]([O:14][C@H:15]([CH2:63][O:64][C:65](=[O:77])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:16][S:17][CH2:18][C@H:19]([NH2:62])[C:20](=[O:61])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:60])[CH:37]([NH2:59])[CH2:38][S:39]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([SiH](C(C)C)C(C)C)(C)C>C(O)(C(F)(F)F)=O>[C:1]([O:14][C@H:15]([CH2:63][O:64][C:65](=[O:77])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:16][S:17][CH2:18][C@H:19]([NH2:62])[C:20](=[O:61])[NH:21][CH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:60])[CH:37]([NH2:59])[CH2:38][SH:39])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 138754Silane, tris(1-methylethyl)-HCID 89428566HCID 89428566, compound

Product 1

HCID 53476668HCID 53476668, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(22R,26R)-4,22-diamino-5,21-dioxo-1,1,1-triphenyl-10,13,16-trioxa-2,24-dithia-6,20-diazaheptacosane-26,27-diyl didodecanoate was stirred in TFA (0.1 M) containing 5% triisopropylsilane at room temperature for 4 hours. The reaction was concentrated and purified by flash chromatography on an ISCO COMBIFLASH® system using a 0-20% MeOH/DCM gradient (20R,24R)-2,20-diamino-1-mercapto-3,19-dioxo-8,11,14-trioxa-22-thia-4,18-diazapentacosane-24,25-diyl didodecanoate. 1H NMR (DMSO d-6): δ 8.51 (t, 1H), 8.49 (t, 1H), 5.12 (m, 1H), 4.26-4.32 (dd, 1H), 4.08-4.12 (m, 1H), 3.86 (q, 2H), 3.46-3.52 (m, 8H), 3.40 (t, 4H), 3.35 (br s, 4H), 3.12-3.25 (m, 4H), 2.82-2.94 (m, 6H), 2.72-2.79 (dd, 1H), 2.29-2.34 (q, 4H), 1.68-1.72 (q, 4H), 1.49-1.52 (m, 4H), 1.21-1.34 (m, 32H), 0.86 (t, 6H). LRMS [M+H]=866.3.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by flash chromatography on an ISCO COMBIFLASH® system

Sources & evidence

ORD record
ord-39982e4db6124a9e957945f78330b6f7
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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