Triethylamine → HCID 178454074, compound

HRID 1257701Notes

Reaction equation

HRID 1257701 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][C:17]([OH:19])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.[OH-].[NH4+]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][C:17](=[O:19])[NH2:22])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 178454076HCID 178454076, compound

Product 1

HCID 178454074HCID 178454074, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of trans (4-tert-butoxycarbonylamino-cyclohexyloxy)-acetic acid (600 mg, 2.20 mmol) and triethylamine (400 μL, 2.90 mmol) in THF (22 mL) at 0° C. was treated dropwise with ethyl chloroformate (250 μL, 2.60 mmol). After 30 minutes ammonium hydroxide (2.20 mL, 170 mmol) was added dropwise. The golden solution was stirred at ambient temperature for 30 minutes and then concentrated under vacuum. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic extracts were washed with 1M HCl, a saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated under vacuum to afford 550 mg (92%) of trans (4-carbamoylmethoxy-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. LCMS (Method Q, ESI): RT=2.82 min, m+H=295.0; 1H NMR (400 MHz, CDCl3) δ: 6.52 (s, 1H), 5.55 (s, 1H), 4.38 (s, 1H), 3.96 (s, 2H), 3.44 (s, 1H), 3.30 (m, 1H), 2.03 (d, 4H), 1.44 (s, 9H), 1.38 (m, 2H), 1.16 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  4. washThe combined organic extracts were washed with 1M HCl
  5. dry with materiala saturated sodium bicarbonate solution and brine, dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ab7758c947024e5ab2eac07aff019ef2
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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