Formic Acid → HCID 22291289, compound

HRID 1467794Notes

Reaction equation

HRID 1467794 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.CN1CC[O:19][CH2:18]C1.C(O)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:18]([NH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[CH:4][CH:3]=1)=[O:19]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl ester

Product 1

HCID 22291289HCID 22291289, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Combined tert-butyl 4-aminobenzoate (15.3 g, 79 mmol), DMAP (1.935 g, 15.84 mmol), N-methylmorpholine (15.67 mL, 143 mmol) in DCM (120 mL) and, after cooling to 0° C., slowly added formic acid (9.11 mL, 238 mmol). After stirring for 18 h, the reaction was concentrated and then partitioned with 1N HCl (100 mL) and EtOAc (200 mL). The aqueous layer was extracted with EtOAc (100 mL). The combined organic layer was washed with brine (50 mL) and dried (MgSO4). The desired product was collected as yellow syrup (16 g).

Workup

  1. concentrationthe reaction was concentrated
  2. custompartitioned with 1N HCl (100 mL) and EtOAc (200 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  4. washThe combined organic layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customThe desired product was collected as yellow syrup (16 g)

Sources & evidence

ORD record
ord-2fd99e67200c466ca75a17864985f3d9
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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