Boron Trichloride → HCID 59608296, compound

HRID 1469621Notes

Reaction equation

HRID 1469621 reaction equation
C([O:8][C:9](=[O:39])[C@H:10]([CH3:38])[CH2:11][C@H:12]([NH:26][C:27]([C:29]1[O:30][CH:31]=[C:32]([O:36][CH3:37])[C:33](=[O:35])[CH:34]=1)=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:19][C:14]([CH2:13][C@@H:12]([NH:26][C:27]([C:29]2[O:30][CH:31]=[C:32]([O:36][CH3:37])[C:33](=[O:35])[CH:34]=2)=[O:28])[CH2:11][C@@H:10]([CH3:38])[C:9]([OH:39])=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 25135Boron Trichloride3×HCID 86648209HCID 86648209, compound

Product 1

HCID 59608296HCID 59608296, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Next, To a solution of (2R,4S)-5-biphenyl-4-yl-4-[(5-methoxy-4-oxo-4H-pyran-2-carbonyl)-amino]-2-methyl-pentanoic acid benzyl ester in methylene chloride (1 mL) is added BCl3 (0.12 mL of a 1M solution in methylene chloride) and the mixture is stirred at room temperature for 18 hours. An additional 0.12 mL of the BCl3 solution is added and stirring is continued for 5 hours. An additional 0.12 mL of the BCl3 solution is added and stirring is continued for 18 hours. The mixture is quenched with water (2 drops) and DMF (1 mL) is added. The solution is purified by preparative HPLC using a gradient of 10% MeCN/water to 100% MeCN (0.1% TFA) to elute the title compound; HPLC Retention time 1.28 minutes (condition C): MS 436.1 (M+1)

Workup

  1. stirringstirring
  2. waitis continued for 5 hours
  3. stirringstirring
  4. waitis continued for 18 hours
  5. customThe mixture is quenched with water (2 drops) and DMF (1 mL)
  6. additionis added
  7. customThe solution is purified by preparative HPLC
  8. washto elute the title compound

Sources & evidence

ORD record
ord-b1d4cfd0c8464fcdb4615dd2291d2eb2
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

Loading…