Sodium Carbonate → cis-2-(Thiophen-2-ylmethoxycarbonylamino)-cyclohexanecarboxylic acid

HRID 990915Notes

Reaction equation

HRID 990915 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C([O-])([O-])=O.[Na+].[Na+].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][O:23][C:24](=O)[O:25]C1C=CC([N+]([O-])=O)=CC=1>O.C1COCC1.Cl>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][O:23][C:24]([NH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9])=[O:25]

Participants

7

Reactant 3

HCID 10340Sodium Carbonate2×HCID 2724640trans-2-Aminocyclohexanecarboxylic acidHCID 697615644-Nitrophenyl thiophen-2-ylmethyl carbonate

Product 1

HCID 70133397cis-2-(Thiophen-2-ylmethoxycarbonylamino)-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Trans-2-amino-1-cyclohexane carboxylic acid (100 mg, 0.7 mmol) in 1 mL of water is added 2M aqueous Na2CO3 until pH=9-10 (2 mL). A solution of the carbonic acid 4-nitro-phenyl ester thiophen-2-ylmethyl ester (195 mg, 0.7 mmol) in THF (1 mL) is added at 0° C. and, after 10 minutes, 1 ml of the 2M Na2CO3 is added to the reaction. The mixture is allowed to warm to RT and vigorously stirred overnight. The reaction mixture is diluted with 0.5N HCl until pH=4-3 and the water layer is extracted three times with CH2Cl2 (10 ml). The organic phases are combined, dried (MgSO4), and concentrated under reduced pressure. The resulting product is used in the next step without further purification.

Workup

  1. extractionthe water layer is extracted three times with CH2Cl2 (10 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting product is used in the next step without further purification

Sources & evidence

ORD record
ord-65fce32f75f242149119773b48a59664
Source dataset
uspto-grants-2002_10
Patent number
US06462076B2

Reaction notes

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