N-(tert-butoxycarbonyl)glycine → HCID 67140164, compound

HRID 1591999Notes

Reaction equation

HRID 1591999 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][N:9]2[S:13](=[O:15])(=[O:14])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[O:25][CH3:26])[C:11](=[O:27])[CH2:10]2)=[CH:6][CH:5]=1.[C:30]([NH:37][CH2:38][C:39](O)=[O:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CCN=C=NCCCN(C)C.Cl>C1COCC1>[C:33]([O:32][C:30](=[O:31])[NH:37][CH2:38][C:39](=[O:40])[NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:10][C:11](=[O:27])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[O:25][CH3:26])[S:13]2(=[O:14])=[O:15])=[CH:28][CH:29]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67138330HCID 67138330, compound

Product 1

HCID 67140164HCID 67140164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title B compound, 5-(4-aminomethyl-benzyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one hydrochloride (89 mg, 0.20 mmol) is suspended in dry THF (10 mL) and N-Boc glycine (42 mg, 0.24 mmol) is added. EDCl (58 mg, 0.30 mmol) is added, followed by TEA (61 mg, 0.60 mmol). The mixture is stirred at RT for 16 h. The solvent is evaporated and the residue is chromatographed on silica gel using CH2Cl2→g 3% MeOH in CH2Cl2 as the eluent to afford ({4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-benzylcarbamoyl}-methyl)-carbamic acid t-butyl ester as a white solid: [M+NH4]+=580.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-70afce6f334d42a7a3a52ab5c1bb5e04
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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