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Benzyl Alcohol → HCID 86747858, compound

HRID 1077956
Notes
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Reaction equation

HRID 1077956 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12](=[O:46])[C@@H:13]([CH3:45])[NH:14][C:15](=[O:44])[C@@H:16]([CH2:25][CH2:26][CH2:27][CH:28]([C:40]([O:42][CH3:43])=[O:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:6][CH:5]=1)([O-])=O.C(O)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C1COCC1>[C:7]1([CH2:10][O:11][C:12](=[O:46])[C@@H:13]([CH3:45])[NH:14][C:15](=[O:44])[C@@H:16]([CH2:25][CH2:26][CH2:27][CH:28]([C:40]([O:42][CH2:43][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[NH:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 86747859N-[N2-[(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)-carbonyl]-(R)-6-[(methoxy)carbonyl]-L-lysyl]-D-alanine 4-nitrophenylmethyl ester

Product 1

HCID 86747858HCID 86747858, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of N-[N2 -[(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)-carbonyl]-(R)-6-[(methoxy)carbonyl]-L-lysyl]-D-alanine 4-nitrophenylmethyl ester (40a, Kolodziejczyk, et. al., Int. J. Pept. Prot. Res., 1992, 39, 382; 683 mg, 1.06 mmol), 4-- molecular sieves (2.15 g, crushed), THF (10.5 mL), and benzyl alcohol (11.0 mL, 105.6 mmol) is stirred for 30 min and then treated with titanium(IV) isopropoxide (82 μl, 0.27 meq). The resulting mixture is heated for 24 h at 85°-90° C. The solids are filtered through diatomaceous earth and the solvent removed. The excess benzyl alcohol is removed by distillation on a Kugelrohr apparatus (approx. 1000μ pressure, 50°-75° C.). The crude orange oil is chromatographed (2.5×31 cm column), gradient of 4:1-2:1 hexane/EtOAc) to provide 40b (633 mg, 88% yield): NMR δ 1.39 (d, J=7.2, 3 H), 1.43 (s, 9 H), 1.40-1.67 (m, 4 H), 1.84 (br s, 2 H), 4.07 (br s, 1 H), 4.40 (m, 1 H), 4.58 (apparent quintet, 1 H), 5.0 (br d, 1 H), 5.07-5.25 (m, 6 H), 5.43 (br d, J=7.9, 1 H), 6.68 (br d, 1 H), 7.33 (m); MS (HR-FAB) m/z 676.3232 (M+H, calcd. for C37H46N3O9, 676.3234).

Workup

  1. temperatureThe resulting mixture is heated for 24 h at 85°-90° C
  2. filtrationThe solids are filtered through diatomaceous earth
  3. customthe solvent removed
  4. customThe excess benzyl alcohol is removed by distillation on a Kugelrohr apparatus (approx. 1000μ pressure, 50°-75° C.)
  5. customThe crude orange oil is chromatographed (2.5×31 cm column), gradient of 4:1-2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-c77c4dbac7144d44b664d0a5a1f5b9c4
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05545662

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes