Diisopropylethylamine → 2-[3-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic acid

HRID 2361123Notes

Reaction equation

HRID 2361123 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.[CH2:49]([O:51][C:52](=[O:64])[C@H:53]([OH:63])[C@H:54]([NH2:62])[CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH3:50]>C(Cl)Cl>[CH2:55]([C@@H:54]([NH:62][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])[C@H:53]([C:52]([O:51][CH2:49][CH3:50])=[O:64])[OH:63])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

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 66864291(2R,3R)-3-amino-2-hydroxy-4-phenyl-butyric acid ethyl ester

Product 1

HCID 710738542-[3-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-propyl]-benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Carboxy-propyl)benzoic acid (69.9 mg, 336 μmol, 1.0 eq.) was combined with DIPEA (187 μL, 3.2 eq.) and HATU (128 mg, 336 μmol, 1.0 eq.) in DCM (7 mL). (2R,3R)-3-Amino-2-hydroxy-4-phenyl-butyric acid ethyl ester (75 mg, 340 μmol, 1.0 eq.) was added and the resulting mixture was stirred for 1 hour. The reaction was quenched by adding saturated NH4Cl and the product was extracted with DCM, dried, and evaporated. One third of the crude product (was dissolved in AcOH (1 mL) and purified by preparative HPLC to yield the title compound (12 mg, 95% purity). MS m/z [M+H]+ calc'd for C23H27NO6, 414.18. found 414.2.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated NH4Cl
  3. extractionthe product was extracted with DCM
  4. customdried
  5. customevaporated
  6. dissolutionOne third of the crude product (was dissolved in AcOH (1 mL)
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7b2a3360acf44ac6812c843d0243e4a9
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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