Reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH2:10][C@@H:11]([OH:15])[C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=1)=O.[C:18]([CH:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C.C([BH3-])#N.[Na+]>CN1CCCC1=O.COC(OC)OC.CO>[C:18]([CH:22]1[CH2:23][CH2:24][CH:25]([NH:28][CH2:1][C:3]2[CH:17]=[CH:16][C:6]([C:7]([NH:9][CH2:10][C@@H:11]([OH:15])[C:12]([OH:14])=[O:13])=[O:8])=[CH:5][CH:4]=2)[CH2:26][CH2:27]1)([CH3:21])([CH3:19])[CH3:20]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
The above resin bound (R)-3-(4-formylbenzoylamino)-2-hydroxypropionic acid was treated with a 0.5 M solution of 4-tert-butylcyclohexylamine (0.25 mmol) in a mixture of N-methyl-2-pyrrolidinone and trimethylorthoformate (1:1, 0.5 mL) and glacial acetic acid (50 μL) for 1 hour at 25° C. Sodium cyanoborohydride (250 μmol, 16 mg) dissolved in a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 0.25 mL) was added and the mixture was vortexed at 25° C. for 4 hours followed by filtration and washing with a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 2×1 mL) 3×1 mL N-methyl-2-pyrrolidinone (3×1 mL) and a mixture of 1,2-dichloropropane and diisopropylethylamine (7:1, 2×0.75 mL).
Workup
- additionwas added
- filtrationfollowed by filtration
- washwashing with a mixture of N-methyl-2-pyrrolidinone and methanol (1:1, 2×1 mL) 3×1 mL N-methyl-2-pyrrolidinone (3×1 mL)
- additiona mixture of 1,2-dichloropropane and diisopropylethylamine (7:1, 2×0.75 mL)
Sources & evidence
- ORD record
- ord-fa4a1c5ab51e473fb5cb99043408e8c8
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562807B2
Linked notes
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