Hydrochloric Acid → HCID 14630194, compound

HRID 2419491Notes

Reaction equation

HRID 2419491 reaction equation
Cl.[NH2:2][C@H:3]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:27][C:28](ON1C(=O)CCC1=O)=[O:29]>CN(C=O)C.CCN(CC)CC>[NH:26]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:27][C:28]([NH:2][C@H:3]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:29]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 3037947L-Glutamic acid dibenzyl ester

Product 1

HCID 14630194HCID 14630194, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution at 0° C, of HCl.H-Glu(OBzl)-OBzl (1.82 g, 5 mmol) in DMF (35 ml), Et3N (0.7 ml) was added dropwise followed by Boc-Gly-OSu (1.5 g, 5.5 mmol). The mixture was stirrred at 0° C for 2 hr and at room temperature overnight; pH 8 was maintained by addition of a few drops of Et3N. The reaction mixture was then evaporated to a small volume and H2O was added. The precipitated oil was extracted with EtOAc and the organic phase was washed with 1 M AcOH, water, and dried (Na2SO4). Evaporation provided an oil which was purified on a Silica gel 60 column using CHCl3 :MeOH (5:1) as eluant. The pooled fractions containing (XVIII) were evaporated yielding colorless oil which failed to crystallize, 1.62 g (67%) homogeneous on tlc [α]D25 -15.0° (c 2, MeOH). Anal. Calcd for C26H32N2O7 (484.558): C, 64.45; H, 6.66; N, 5.78. Found: C, 64.23; H, 6.72; N, 5.66. Compound XVIII was also prepared from Boc-Gly-Glu(OBzl)-OH via the cesium salt procedure of Wang et al, supra.

Workup

  1. customat 0° C
  2. customThe reaction mixture was then evaporated to a small volume and H2O
  3. additionwas added
  4. extractionThe precipitated oil was extracted with EtOAc
  5. washthe organic phase was washed with 1 M AcOH, water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation
  8. customprovided an oil which
  9. customwas purified on a Silica gel 60 column
  10. additionThe pooled fractions containing (XVIII)
  11. customwere evaporated
  12. customyielding colorless oil which
  13. customto crystallize
  14. customCompound XVIII was also prepared from Boc-Gly-Glu(OBzl)-OH via the cesium salt procedure of Wang et al, supra

Sources & evidence

ORD record
ord-9d14716f3c7e4cbc935e3c32b8a7a6c4
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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