Water → HCID 66832530, compound

HRID 1914518Notes

Reaction equation

HRID 1914518 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.[N:23]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=N1.C(N(CC)CC)C.O.C(Cl)[Cl:52]>>[C:4]([O:3][C:1]([N:8]1[CH2:15][CH2:14][CH2:13][CH:9]1[C:10](=[O:12])[NH:25][CH2:26][C:31]1[CH:30]=[C:29]([Cl:52])[CH:28]=[CH:27][N:23]=1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 66832530HCID 66832530, compoundYield 93%

Procedure

To a solution of N-boc-L-proline (0.50 g, 2.3 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1.02 g, 2.3 mmol) in DCM was added triethylamine (1.40 g, 13.8 mmol) and the reaction mixture was stirred for 30 minutes. C-(4-Chloro-pyridin-2-yl)-methylamine dihydrogenchloride (0.50 g, 2.30 mmol) was added and the reaction mixture was stirred for 12 hours. Water was added and the reaction mixture was extracted with DCM. The organic layers were combined, dried with Na2SO4, filtered, concentrated and purified by FCC (0-60% EtOAc in hexane) to provide the desired product (0.93 g, 93%). 1H NMR (400 MHz, DMSO) δ 8.62-8.51 (m, 1H), 8.47 (dd, J=9.8, 5.3, 1H), 7.56-7.31 (m, 2H), 4.45-4.27 (m, 2H), 4.20-4.09 (m, 1H), 3.51-3.24 (m, 2H), 2.26-2.05 (m, 1H), 1.95-1.69 (m, 3H), 1.48-1.24 (m, 9H).

Workup

  1. stirringthe reaction mixture was stirred for 12 hours
  2. extractionthe reaction mixture was extracted with DCM
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by FCC (0-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-31f97fade537411889024b477fe5cdcf
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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