Diisopropylethylamine → HCID 71074972, compound

HRID 2361131Notes

Reaction equation

HRID 2361131 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([OH:3])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O:51][C:52](=[O:64])[CH2:53][C@H:54]([NH2:63])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[Cl:62])C>C(Cl)Cl>[C:52]([CH2:53][C@H:54]([NH:63][C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:3])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[Cl:62])([OH:64])=[O:51]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 124220832-(3-Carboxypropyl)benzoic acidHCID 71073521HCID 71073521, compound

Product 1

HCID 71074972HCID 71074972, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Carboxy-propyl)benzoic acid (160 mg, 790 μmol, 1.0 eq.), DIPEA (439 μL, 3.2 eq.) and HATU (300 mg, 788 μmol, 1.0 eq.) were combined in DCM (20 mL) and stirred for 5 minutes at room temperature. (R)-3-amino-4-(2-chloro-phenyl)-butyric acid ethyl ester (200 mg, 827 μmol, 1.1 eq.) was added and the resulting mixture was stirred for 1 hour. The reaction was quenched with saturated NH4Cl, and the product was extracted with DCM, dried and evaporated. THF (20 mL) and 10 M aqueous NaOH (315 μL) was added and the mixture was stirred for 1 hour. The crude material was dissolved in AcOH (1.5 mL) and purified using preparative HPLC to yield the title compound (25 mg, 95% purity). MS m/z [M+H]+ calc'd for C21H22ClNO5, 404.12. found 404.4.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. customThe reaction was quenched with saturated NH4Cl
  3. extractionthe product was extracted with DCM
  4. customdried
  5. customevaporated
  6. additionTHF (20 mL) and 10 M aqueous NaOH (315 μL) was added
  7. stirringthe mixture was stirred for 1 hour
  8. dissolutionThe crude material was dissolved in AcOH (1.5 mL)
  9. custompurified

Sources & evidence

ORD record
ord-213e63809a714e428bb439d37b3c38ed
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

Loading…