Dimethylformamide → Indanylglycine Val-OAllyl

HRID 1631427Notes

Reaction equation

HRID 1631427 reaction equation
C([N:18]([CH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][C:20]([OH:22])=[O:21])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH2:32][C@H:33]([C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])[CH:34]([CH3:36])[CH3:35].CN(C=O)C.N1CCCCC1>C(Cl)Cl>[CH:23]1([NH:18][CH2:19][C:20]([OH:22])=[O:21])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.[NH2:32][C@H:33]([C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])[CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 131731716Fmoc-Indanylglycine Val-OAllyl

Product 1

HCID 131731717Indanylglycine Val-OAllylYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fmoc-Indanylglycine-Val-OAllyl (0.758 g, 1.31 mmol) was solvated in CH2Cl2 (5 mL) and DMF (1.8 mL) followed by dropwise addition of piperidine (1.05 mL, 8.1 eq) over 30 seconds. After 45 min, the mixture was subjected to extraction CH2Cl2/brine (30/15 mL) and saturated NH4Cl (5 mL). The organic layer was dried over MgSO4, concentrates and purified by silica using a gradient of MeOH/CH2Cl2 (0 to 5%) to get 0.45 g of the desired compound.

Workup

  1. extractionthe mixture was subjected to extraction CH2Cl2/brine (30/15 mL) and saturated NH4Cl (5 mL)
  2. dry with materialThe organic layer was dried over MgSO4, concentrates
  3. custompurified by silica using a gradient of MeOH/CH2Cl2 (0 to 5%)

Sources & evidence

ORD record
ord-e4ce9f32464447c8a960ae660b80942b
Source dataset
uspto-grants-2014_07
Patent number
US08791235B2

Reaction notes

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