Triethylamine → HCID 178453994, compound

HRID 2089039Notes

Reaction equation

HRID 2089039 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32]C)[CH:30]=3)[N:25]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:24]=2)[CH:3]=1.B(Br)(Br)Br.C(N(CC)CC)C.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[N:25]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:24]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25134Boron tribromideHCID 90495Di-tert-butyl dicarbonateHCID 178493666HCID 178493666, compound

Product 1

HCID 178453994HCID 178453994, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 213d (0.927 g, 1.514 mmol) in CH2Cl2 (50 mL) was added 1M BBr3 in CH2Cl2 (10.6 mL, 10.6 mmol) at −78° C. The reaction was slowly warmed to room temperature and stirred overnight. The solvent was evaporated. To a suspension of the residue in THF (60.0 mL) was added triethylamine (1.48 mL, 10.6 mmol) and Boc2O (0.380 g, 1.74 mmol). The reaction was stirred for 8 hours, diluted with 50% brine, and extracted with EtOAc. The organic layers was dried over MgSO4, filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc to give the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionTo a suspension of the residue in THF (60.0 mL)
  3. stirringThe reaction was stirred for 8 hours
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layers was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on a 40 g column
  9. washeluting with CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-00db2ef7639e48c3ba9385bacea64c2a
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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