Hydrazine → (S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester

HRID 1039032Notes

Reaction equation

HRID 1039032 reaction equation
[NH2:1][C:2](=O)[CH2:3][C@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.NN>O1CCCC1>[CH2:8]([O:7][C:5](=[O:6])[C@@H:4]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:3][C:2](=[S:33])[NH2:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 87949Lawesson's reagentHCID 14420402Benzyl N~2~-(tert-butoxycarbonyl)-L-asparaginate

Product 1

HCID 86654757(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1-L round bottom flask was charged with (S)-benzyl 4-amino-2-(tert-butoxycarbonylamino)-4-oxobutanoate (10.0 g, 31.0 mmol), Lawesson's reagent (6.58 g, 16.3 mmol), and tetrahydrofuran (155 mL). Hydrazine (7.8 mL, 0.248 mol) was added and the resulting mixture was stirred at room temperature for 72 h. The resulting mixture was then concentrated in vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF40-400 g column, gradient 90:10-60:40 Heptane:EtOAc) to yield-(S)-tert-butoxycarbonylamino-3-thiocarbamoyl-propionic acid benzyl ester. MS (ES+) 339 (M+1).

Workup

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue purified via flash silica gel chromatography (Analogix IF-280

Sources & evidence

ORD record
ord-3543d5515422496ba01160057b056898
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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