HCID 18606052, compound → HCID 18606036, compound

HRID 979966Notes

Reaction equation

HRID 979966 reaction equation
C([O:5][C:6](=[O:31])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:30])[N:13]([CH3:29])[NH:14][CH:15]([C:24]([O:26]CC)=[O:25])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(C)(C)C>FC(F)(F)C(O)=O>[C:24]([CH:15]([NH:14][N:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:31])=[O:5])=[O:30])[CH3:29])[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([OH:26])=[O:25]

Participants

3

Reactant 1

HCID 18606052HCID 18606052, compound

Product 1

HCID 18606036HCID 18606036, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A soluion of azapeptide 16S (more mobile diastereomer; (0.335 g; 0.774 mmol) in trifluoroacetic acid (5 ml) was allowed to stand for 3 hours. The reside after evaporation wa combined with sodium hydroxide (1 N; 3 ml) and THF (0.5 ml) and the resulting solution was stirred under nitrogen for 18 hrs. After neutralization with dilute hydrochloric acid, the solution was placed onto a column of DOWEX 50W-X4 ion-exchange resin (5 g). The product wa eluted with 20:1 H2O-pyr and freeze-dried to a white foam (0.215 g; 0.1=616 mmol; 80%). A portion of this material (0.052 g) was purified by chromatography on silica gel (85:30:5:1 CHCl3 -CH3OH-H2O:HOAc), affording pure product (0.031 g). The disodium salt (0.025 g) precipitated from CH2Cl2 ; m.p. 220-225 (dec). TLC (silica gel; 10:5:1:3 EPAW) Rf=0.45. Analysis: Calculated for C17H23N3O 5 . 2Na: C, 51.65; H, 5.82; N, 10.63. Found: C, 51.54; H, 5.79; N, 10.28. MS (for diacid): m/e 403 (monotrimethylsilyl of M+ -H2O). NMR (CDCl3). 1.7-2.3 (6H, m); 2.6-2.8 (2H, m); 3.00 (3H, s); 3.5-3.6 (3H, m); 4.3-4.5 (1H, m); 7.1-7.3 (5H, m); 7.4-8.0 (2H, broad).

Workup

  1. customThe reside after evaporation
  2. washThe product wa eluted with 20:1 H2O-pyr
  3. customfreeze-dried to a white foam (0.215 g; 0.1=616 mmol; 80%)
  4. customA portion of this material (0.052 g) was purified by chromatography on silica gel (85:30:5:1 CHCl3 -CH3OH-H2O:HOAc)

Sources & evidence

ORD record
ord-00512a6e56ea4e639f019358f68c345c
Source dataset
uspto-grants-1987_01
Patent number
US04634715

Reaction notes

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