Dimethylformamide → HCID 86753218, compound

HRID 399522Notes

Reaction equation

HRID 399522 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@@H:10](N)[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26]([NH:28][C:29](=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])SC)=[O:27])([CH3:24])([CH3:23])[CH3:22].C[N:41](C)C=O>C(OCC)C>[C:1]([O:5][C:6](=[O:20])[C@@H:7]1[CH2:11][C@H:10]([N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:29]([NH2:41])=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 54009054HCID 54009054, compound

Product 1

HCID 86753218HCID 86753218, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (4R)-1-(tert-butyloxycarbonyl)-4-amino-L-proline tert-butyl ester (134 mg, 0.468 mmol) and N,N'-bis(tert-butyloxycarbonyl)-S-methyl-isothiourea (150 mg, 0.515 mmol) in N,N-dimethylformamide (2 mL) was heated for 15 hours at 55° C. and 2 days at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with diethyl ether, washed with water, dried (Na2SO4), and evaporated. The title compound was obtained pure by flash silica gel chromatography eluting with 10% ethyl acetate/hexane; yield 60.2 mg (24%). Mass spectrum: m/z 529 (M+1); 400 MHz 1H NMR (CD3OD): δ1.44-1.52 (4s, 36H); 2.08 (m, 1H); 2.59 (m, 1H); 3.42 (m, 1H); 3.78 (m, 1H); 4.23 (dd, 1H); 4.57 (m, 1H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-0bf9d538a88e40369584e2541a58194c
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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