Diisopropylethylamine → (S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate

HRID 333133Notes

Reaction equation

HRID 333133 reaction equation
[NH2:1][C@H:2]([C:9]([NH:11][C@@H:12]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1)=[O:14])=[O:10])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[N:30]([C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1)=[C:31]=[S:32].CCN(C(C)C)C(C)C>C(#N)C>[I:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[C@@H:2]([NH:1][C:31]([NH:30][C:33]2[CH:34]=[CH:35][C:36]([S:39](=[O:41])(=[O:40])[NH2:42])=[CH:37][CH:38]=2)=[S:32])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213594-IsothiocyanatobenzenesulfonamideHCID 68632742(S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate

Product 1

HCID 86632285(S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-methyl 4-(tert-butoxycarbonylamino)-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate (0.448 g, 0.723 mmol) in DCM (10 mL) and TFA (4.0 mL) was stirred at room temperature overnight. After the solvent was evaporated, the reaction mixture was diluted with DCM, washed with sat. K2CO3 and concentrated in vacuo to afford (S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate. A solution of the above product ((S)-methyl 4-amino-5-((S)-1-(4-iodobenzylamino)-5-methoxy-1,5-dioxopentan-2-ylamino)-5-oxopentanoate), 4-isothiocyanatobenzenesulfonamide (0.171 g, 0.80 mmol) in acetonitrile (10 mL) containing DIPEA (0.40 mL) was stirred at room temperature under nitrogen for 48 h. The solvent was evaporated under reduced pressure to give a crude product, which was purified by flash chromatography 5% MeOH in DCM as eluent to give (S)-methyl 5-(4-iodobenzylamino)-4-((S)-5-methoxy-5-oxo-2-(3-(4-sulfamoylphenyl)thioureido)pentanamido)-5-oxopentanoate (0.469 g) as a white solid. MS (ESI), 756 (M+Na)+, 377 (M/2+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give a crude product, which
  3. customwas purified by flash chromatography 5% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-ff1e856f9c3c4098ae9902dea324907f
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

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