HCID 69707452, compound → HCID 69706609, compound

HRID 2414377Notes

Reaction equation

HRID 2414377 reaction equation
C(OC([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[N:25]([CH2:26][CH2:27][C:28]#[N:29])[N:24]=[N:23][N:22]=2)[CH:16]=1)[C:10]#[N:11])=O)(C)(C)C>C(O)=O>[NH2:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[N:25]([CH2:26][CH2:27][C:28]#[N:29])[N:24]=[N:23][N:22]=2)[CH:16]=1)[C:10]#[N:11]

Participants

3

Reactant 1

HCID 69707452HCID 69707452, compound

Product 1

HCID 69706609HCID 69706609, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (S)-2-t-butoxycarbonylamino-3-{3-[1-(2-cyanoethyl)-5-tetrazolyl]-benzyloxy}-propionitrile (3.49 g, 8.8 mmol) in formic acid (22 mL) is stirred at room temp. for 6 h., after which time the formic acid is evaporated at 25° C. The residue is then dissolved in water (50 mL), basified with sat'd aqueous NaHCO3, and extracted with ethyl acetate (3×150 mL). The combined organic layers are then washed with water (50 mL), brine (50 mL), dried (MgSO4) and evaporated to yield (S)-2-amino-3-{3-[1-(2-cyanoethyl)-5-tetrazolyl]-benzyloxy}-propionitrile, as a light yellow oil, which is utilized without further purification.

Workup

  1. customafter which time the formic acid is evaporated at 25° C
  2. dissolutionThe residue is then dissolved in water (50 mL)
  3. extractionextracted with ethyl acetate (3×150 mL)
  4. washThe combined organic layers are then washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0c7fd550c92c441dbbe402c7639b463c
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

Loading…