Hydrochloric Acid → GlcA Ile-Phe-OBzl

HRID 256462

Reaction equation

HRID 256462 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5].C(N(CC)CC)C.[CH2:36]([OH:47])[C@H:37]1[O:43][C:41](=[O:42])[C@H:40]([OH:44])[C@@H:39]([OH:45])[C@@H:38]1[OH:46]>CN(C=O)C>[OH:42][CH:41]1[O:43][C@H:37]([C:36](=[O:9])[OH:47])[C@@H:38]([OH:46])[C@H:39]([OH:45])[C@H:40]1[OH:44].[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:9])[C@H:4]([CH2:6][CH3:7])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7027delta-GluconolactoneHCID 8471TriethylamineHCID 131715370H-Ile-Phe-OBzl

Product 1

HCID 131715369GlcA Ile-Phe-OBzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of HCl, H-Ile-Phe-OBzl (1.41 g, 3.5 mmol) in freshly distilled DMF (2 ml) neutralized with triethylamine (0.49 ml, 3.5 mmol), δ-gluconolactone (1.25 g, 7 mmol) and TEA (0.98 ml, 7 mmol) were added. The mixture was stirred at 60° C. for 24 hr. δ-gluconolactane (0.63 g, 3.5 mmol) and TEA (0.43 ml, 3.5 mmol) were then added and the mixture was stirred for 24 h more. The mixture was then filtered and the filtrate evaporated under reduced pressure. The residue was purified by preparative chromatography on a silica gel column eluted with the system chloroform-methanol-water (16:6:1): yield 1.1 g (58%) after precipitation in ether-petroleum ether (1:1, v/v); mp 175°-176° C.; [α]54625 =+1.3° (c=1, DMF); Rf(A) =0.53.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 24 h more
  3. filtrationThe mixture was then filtered
  4. customthe filtrate evaporated under reduced pressure
  5. customThe residue was purified by preparative chromatography on a silica gel column
  6. washeluted with the system chloroform-methanol-water (16:6:1)
  7. customyield 1.1 g (58%) after precipitation in ether-petroleum ether (1:1
  8. custom[α]54625 =+1.3° (c=1, DMF)

Sources & evidence

ORD record
ord-741ca17ff3524c10a2c68a446879c760
Source dataset
uspto-grants-1987_10
Patent number
US04703107

Linked notes

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