Ammonium Chloride → ((1R,3R)-3-carbamoyl-cyclopentyl)-carbamic acid tert-butyl ester

HRID 245857Notes

Reaction equation

HRID 245857 reaction equation
[C:1]([NH:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([OH:16])=O)[CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl-].[NH4+].C[N:20](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14](=[O:16])[NH2:20])[CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 1512527(1R,3R)-3-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71280595((1R,3R)-3-carbamoyl-cyclopentyl)-carbamic acid tert-butyl esterYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, (1R,3R)—N-Boc-1-aminocyclopentane-3-carboxylic acid (300 mg, 1.31 mmol) and ammonium chloride (210 mg, 3.93 mmol) were suspended in DMF (6 ml). HATU (547 mg, 1.44 mmol) and N,N-diisopropylethylamine (0.80 ml, 4.58 mmol) were added and the yellow suspension was stirred at room temperature for 72 h. The reaction mixture was quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated to afford 97 mg (33%) of ((1R,3R)-3-carbamoyl-cyclopentyl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-774a084954f640a69eb04359e99bad39
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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