Benzoic Acid → HCID 60207250, compound

HRID 493363Notes

Reaction equation

HRID 493363 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[C:29]([O:33][C:34]([NH:36][C@@H:37]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:49]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:48]=1)[C:38]([O:40][C@H:41]([CH3:45])[C@H:42](O)[CH3:43])=[O:39])=[O:35])([CH3:32])([CH3:31])[CH3:30]>ClCCl.CN(C)C1C=CN=CC=1>[C:29]([O:33][C:34]([NH:36][C@@H:37]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:49]([O:61][CH2:62][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:48]=1)[C:38]([O:40][C@H:41]([CH3:45])[C@H:42]([O:8][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])[CH3:43])=[O:39])=[O:35])([CH3:31])([CH3:32])[CH3:30]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 60207249HCID 60207249, compound

Product 1

HCID 60207250HCID 60207250, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzoic acid (0.57 g, 4.8 mmol) in anhydrous dichloromethane was added triethylamine (1.7 mL, 12 mmol), and 2,4,6-trichlorobenzoyl chloride (0.9 mL, 5.76 mmol) were added. The resulting mixture was stirred for 30 min and a solution of (1R,2R)-2-hydroxy-1-methylpropyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (2.4 g, 4.4 mmol) in dichloromethane was slowly added to the reaction mixture, followed by the addition of a catalytic amount of 4-(dimethylamino)pyridine. The resulting mixture was stirred at room temperature for 16 hrs, washed with 10% citric acid, dried over Na2SO4, and concentrated. Chromatography (silica gel, 20% ethyl acetate in hexane) of the residue afforded 2.6 g (90%) of (1R,2R)-1-Methyl-2-phenylcarbonyloxypropyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate. 1H NMR (400 MHz, CDCl3): δ 1.26 (d, J=6.4 Hz, 6H), 1.39 (s, 9H), 2.78 (m, 1H), 2.96 (m, 1H), 4.51 (m, 1H), 4.89 (d, 1H), 5.10 (s, 4H), 5.15 (m, 1H), 6.57 (d, J=8 Hz, 1H), 6.71 (s, 1H), 6.77 (d, J=8 Hz, 1H), 7.25-7.43 (m, 12H), 7.52 (t, J=7.6 Hz, 1H), 7.99 (d, J=7.6 Hz, 2H).

Workup

  1. additionwere added
  2. stirringThe resulting mixture was stirred at room temperature for 16 hrs
  3. washwashed with 10% citric acid
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd6ba95ad5654a8594d4c04c1fde8d1e
Source dataset
uspto-grants-2009_05
Patent number
US07534813B2

Reaction notes

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