Neopentylamine → HCID 178449110, compound

HRID 1158259Notes

Reaction equation

HRID 1158259 reaction equation
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:45])[NH:11][CH:12]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:13]([OH:37])[CH2:14][N:15]([S:20]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[C:26]3=[CH:33][N:34]([CH3:36])C)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.[CH2:46](N)[C:47](C)([CH3:49])[CH3:48]>C(O)C>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:45])[NH:11][CH:12]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:13]([OH:37])[CH2:14][N:15]([S:20]([C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][C:27](=[O:32])[C:26]3=[CH:33][NH:34][CH2:36][C:47]([CH3:49])([CH3:48])[CH3:46])(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:2]1

Participants

4

Reactant 2

HCID 79882NeopentylamineHCID 67371409{1-Benzyl-3-[(3-dimethylaminomethylene-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

Product 1

HCID 178449110HCID 178449110, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {1-benzyl-3-[(3-dimethylaminomethylene-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 21 (32mg, 0.05 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 μl, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20×20 cm, 500 μm) using 8:2 ethyl acetate:hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 22 (24 mg, 70%). TLC: Rf 0.63 (ethyl acetate:hexanes). MS m/z 685 (MH)+. 1H NMR (CDCl3) is consistent with structure.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified on a preparative TLC plate (20×20 cm, 500 μm)

Sources & evidence

ORD record
ord-660331e221604acea1ecc804241ba0ec
Source dataset
uspto-grants-2010_10
Patent number
US07807845B2

Reaction notes

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