Citric Acid → HCID 70172695, compound

HRID 2306268Notes

Reaction equation

HRID 2306268 reaction equation
[CH:1]([Si:4]([O:11][C:12](=[O:36])[N:13]([CH2:19][CH2:20][C:21]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([F:35])[CH:28]=2)[CH:24]=[N:23][CH:22]=1)[C@H:14]1[CH2:18][CH2:17][NH:16][CH2:15]1)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH:37]([Si:40]([CH:58]([CH3:60])[CH3:59])([CH:55]([CH3:57])[CH3:56])[O:41][C:42]1[CH:51]=[C:50]2[C:45]([CH:46]=[CH:47][CH:48]=[C:49]2[C:52](O)=[O:53])=[CH:44][CH:43]=1)([CH3:39])[CH3:38].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH:1]([Si:4]([O:11][C:12](=[O:36])[N:13]([CH2:19][CH2:20][C:21]1[N:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([F:35])[CH:28]=2)[CH:24]=[N:23][CH:22]=1)[C@H:14]1[CH2:18][CH2:17][N:16]([C:52]([C:49]2[C:50]3[C:45](=[CH:44][CH:43]=[C:42]([O:41][Si:40]([CH:55]([CH3:57])[CH3:56])([CH:58]([CH3:60])[CH3:59])[CH:37]([CH3:38])[CH3:39])[CH:51]=3)[CH:46]=[CH:47][CH:48]=2)=[O:53])[CH2:15]1)([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 2724699PyBOPHCID 18536004HCID 18536004, compoundHCID 70171489HCID 70171489, compound

Product 1

HCID 70172695HCID 70172695, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-N-{2-[1-(4-Cyano-3-fluorobenzyl)-1H-imidazol-5-yl]ethyl}-N-(pyrrolidin-3-yl)carbamic acid triisopropylsilyl ester, as described above in Step H, (242 mg, 0.471 mmol), 7-(triisopropylsilyloxy)-1-naphthlenecarboxylic acid, as described in Example 54, Step C, (162 mg, 0.471 mmol), PYBOP (245 mg, 0.471 mmol), and triethylamine (0.085 mL, 0.612 mmol) were combined in CH2Cl2 (4 mL). The reaction mixture was stirred at ambient temperature for 4 hours, then poured into 10% aqueous citric acid and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e208d62116840e983f3a3c750715c24
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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