1,3-Bis(benzyloxycarbonyl)-2-methylisothiourea → HCID 178462146, compound

HRID 366090Notes

Reaction equation

HRID 366090 reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([NH:16][C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH3:18])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:26]([NH:36][C:37](=[N:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])SC)([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>CN(C=O)C>[C:41]([NH:40][C:37](=[N:36][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[NH:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:14]([NH:16][C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH3:18])=[O:15])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2])([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42]

Participants

4

Reactant 2

HCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 131722103(R)-N2-(Boc)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

Product 1

HCID 178462146HCID 178462146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-N2 -(Boc)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide (11.47 g; 0.33 mmol; from step (a) above) in DMF (50 mL) was added N,N'-bis(Cbz)-S-methylisothiourea (11.8 g; 0.33 mmol). The solution was stirred overnight at room temperature followed by removal of the solvent under reduced pressure. The resultant oil was chromatographed on a plug of silica gel (7.5 cm×12.5 cm) eluting first with CH2Cl2 (800 mL) to remove the higher Rf impurities. The eluent was switched to EtOAc (600 mL) to elute the sub-title compound as a white foam (14.67 g).

Workup

  1. customfollowed by removal of the solvent under reduced pressure
  2. customThe resultant oil was chromatographed on a plug of silica gel (7.5 cm×12.5 cm)
  3. washeluting first with CH2Cl2 (800 mL)
  4. customto remove the higher Rf impurities
  5. washto elute the sub-title compound as a white foam (14.67 g)

Sources & evidence

ORD record
ord-4232074c51134ccf81d0bad4d5167258
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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