Diisopropylethylamine → HCID 59868591, compound

HRID 1923993Notes

Reaction equation

HRID 1923993 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[NH2:27][C@@H:28]([CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=1)[C:29]([NH:31][C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:30].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([C:10](=[O:12])[NH:27][C@H:28]([C:29](=[O:30])[NH:31][C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 110110222-((tert-Butoxycarbonyl)amino)-3-ethoxy-3-oxopropanoic acidHCID 59367128HCID 59367128, compound

Product 1

HCID 59868591HCID 59868591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid XCVII (0.5 g; 2.02 mmol) and DIPEA (1.20 mL; 7.07 mM) in DCM (30 mL) was added (2S)-2-amino-N-(quinolin-3-yl)-3-[4-(trifluoromethyl)phenyl]propanamide LXXI (0.88 g; 2.02 mmol) and TBTU (0.68 g; 2.12 mmol). The reaction mixture was stirred overnight, diluted with DCM (30 mL), washed with 1 M aq NaOH (2×), 1 M aqueous HCl (2×), brine and dried over anhydrous MgSO4. The solvent was evaporated and the crude product was crystallized from DCM/hexane to give ethyl 2-{[(tert-butoxy)carbonyl]amino}-2-{[(1S)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamoyl}acetate XCVIII as yellow crystals (0.90 g, 1.53 mmol, 76% yield). ESIMS found for C29H31F3N4O6 m/z 589 (M+H).

Workup

  1. washwashed with 1 M aq NaOH (2×), 1 M aqueous HCl (2×), brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was evaporated
  4. customthe crude product was crystallized from DCM/hexane

Sources & evidence

ORD record
ord-86a870ec584c40b080e9eaa2ec968dcf
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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