Ammonium Chloride → HCID 90036644, compound

HRID 1055394Notes

Reaction equation

HRID 1055394 reaction equation
[NH4+].[Cl-].[CH2:3]([N:10]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:11]([C:15]1([O:21][C:22]2[C:27]([N+:28]([O-])=O)=[CH:26][CH:25]=[C:24]([F:31])[C:23]=2[F:32])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:12]([OH:14])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.[Zn]>[NH2:28][C:27]1[C:22]([O:21][C:15]2([CH:11]([N:10]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:12]([OH:14])=[O:13])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[C:23]([F:32])[C:24]([F:31])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90036829HCID 90036829, compound

Product 1

HCID 90036644HCID 90036644, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

NH4Cl (48.0 mg, 0.90 mmol, Eq: 2) and Zn powder (440 mg, 6.73 mmol, Eq: 15) were added to a solution of 2-(dibenzylamino)-2-(4-(2,3-difluoro-6-nitrophenoxy)tetrahydro-2H-pyran-4-yl)-acetic acid (230 mg, 449 μmol, Eq: 1.00) in MeOH (10 mL) and the mixture was heated to 65° C. After 2 h the mixture was filtered through Celite. The filtrate was concentrated and partitioned between 1 N NaOAc and EtOAc. The organic layer was dried over Na2SO4 then concentrated under reduced pressure to afford [4-(6-amino-2,3-difluoro-phenoxy)-tetrahydro-pyran-4-yl]-dibenzylamino-acetic acid (185 mg) which was used without purification.

Workup

  1. filtrationAfter 2 h the mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between 1 N NaOAc and EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-005b0cb6c041410ea2e88e2ab14b15ce
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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