1-(tert-Butoxycarbonyl)-3-phenylproline → HCID 23560060, compound

HRID 1058326Notes

Reaction equation

HRID 1058326 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O:26][C:27]([NH:29][CH2:30][C:31]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:32]=1[CH2:33][NH:34][C:35](=[O:41])[C@@H:36]1[CH2:40][CH2:39][CH2:38][NH:37]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)CCl>[O:5]([C:6]([N:8]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:9]1[C:10]([N:37]1[CH2:38][CH2:39][CH2:40][C@H:36]1[C:35]([NH:34][CH2:33][C:32]1[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:31]=1[CH2:30][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])=[O:41])=[O:11])=[O:7])[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 47125141-(tert-Butoxycarbonyl)-3-phenylprolineHCID 11428605L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide

Product 1

HCID 23560060HCID 23560060, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(tert-Butoxylcarbonyl)-3-phenylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide was prepared as a mixture of diastereomers from 1-(tert-Butoxycarbonyl)-3-phenyl-D,L-proline (88 mg, 0.30 mmol) from the previous step and L-prolin-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)amide (111 mg, 0.30 mmol) essentially according to the EDC coupling procedure described in Step 3 of Example 46. The diastereomeric products separated under the following analytical conditions: Chiralcel OD (250×4.6 m) column eluting with A/B 85/15 where A=hexane/0. 1% diethylamine and B=ethanol, with detection at 220 nm and flow rate of 1.0 mL/min. Under these conditions, the early peak elutes at 4.87 min. and later peak at 8.51 min. The products were separated on preparative scale using these conditions. Diastereomer A: LCMS RT=2.72 min. LCMS (M+H)=641.2. Diastereomer B: LCMS RT=2.75 min. LCMS (M+H)=641.0

Workup

  1. customThe diastereomeric products separated under the following analytical conditions
  2. washChiralcel OD (250×4.6 m) column eluting with A/B 85/15 where A=hexane/0
  3. waitlater peak at 8.51 min
  4. customThe products were separated on preparative scale

Sources & evidence

ORD record
ord-61355c720bec44e3b77b59bebffcaefd
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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