Piperidine → (R)-3-(4-Formylbenzoylamino)-2-hydroxypropionic acid

HRID 412472

Reaction equation

HRID 412472 reaction equation
C([NH:18][CH2:19][C@H:20]([C:22]([OH:24])=[O:23])[OH:21])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N1CCCCC1.[CH:31]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=O)=[CH:35][CH:34]=1)=[O:32].C1C=CC2N(O)N=NC=2C=1.C(N=C=NC(C)C)(C)C>CN(C=O)C.CN1CCCC1=O.C(#N)C>[CH:31]([C:33]1[CH:34]=[CH:35][C:36]([C:37]([NH:18][CH2:19][C@@H:20]([OH:21])[C:22]([OH:24])=[O:23])=[O:39])=[CH:40][CH:41]=1)=[O:32]

Participants

9

Reactant 5

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7408673(R)-Fmoc-isoserine

Product 1

HCID 86586064(R)-3-(4-Formylbenzoylamino)-2-hydroxypropionic acid

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the above resin bound (R)-Fmoc-isoserine was added 500 μL of a 20% solution of piperidine in DMF. Upon shaking for 30 min, the resin was drained and washed with N-methyl-2-pyrrolidinone (6×1 mL). Then, 200 μmol 4-formylbenzoic acid (30 mg) and 200 μmol HOBt (31 mg) was dissolved in N-methyl-2-pyrrolidinone (500 μL) and added to the resin followed by 200 μmol diisopropyl carbodiimide (25.2 mg) dissolved in acetonitrile (500 μL). The mixture was shaken for 4 hours at 25° C. followed by filtration and washing of the resin with N-methyl-2-pyrrolidinone (3×1 mL).

Workup

  1. washwashed with N-methyl-2-pyrrolidinone (6×1 mL)
  2. additionadded to the resin
  3. stirringThe mixture was shaken for 4 hours at 25° C.
  4. filtrationfollowed by filtration
  5. washwashing of the resin with N-methyl-2-pyrrolidinone (3×1 mL)

Sources & evidence

ORD record
ord-fe41ed78558740f381eb97a1989fd813
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Linked notes

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