Boc-Pro-Gly-Gly-Gly-OCH2Ph → Pro-Gly-Gly-Gly-OCH2Ph

HRID 1246737Notes

Reaction equation

HRID 1246737 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:27][CH2:26][CH2:25][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:12])=[O:8])=[O:4]>Cl.O1CCOCC1>[NH:1]1[CH2:27][CH2:26][CH2:25][C@H:2]1[C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:12])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 131726008Boc-Pro-Gly-Gly-Gly-OCH2Ph

Product 1

HCID 101169634Pro-Gly-Gly-Gly-OCH2Ph

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Boc-Pro-Gly-Gly-Gly-OCH2Ph (SEQ ID NO.: 1) (0.2 g, 0.42 mmol) was dissolved in a 4N HCl solution in dioxane (10 mL) at 5° C. and the reaction mixture was stirred for 1 h at room temperature. The solvent was evaporated and the residue carefully dried at high vacuum and then crystallized from MeOH/Et2O to give Pro-Gly-Gly-Gly-OCH2Ph (SEQ ID NO.: 1) (0.18 g, 100%) as a colorless solid, mp 145–146° C. 1H-NMR (300 MHz, δ, CD3OD): 2.00–2.25 (4H, m), 3.35–3.45 (2H, m), 3.90–4.05 (6H, m), 4.30–4.40 (1H, m), 5.18 (2H, s), 7.30–7.40 (5H, m). 13C-NMR (75 MHz, δ, CD3OD): 25.2, 30.9, 42.1, 43.3, 43.7, 47.6, 61.4, 68.1, 129.5, 129.6, 129.9, 137.5, 170.9, 171.4, 171.8, 172.4.

Workup

  1. customThe solvent was evaporated
  2. customthe residue carefully dried at high vacuum
  3. customcrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-2adf54c9ab2640d5b39ef78bbda4c200
Source dataset
uspto-grants-2006_10
Patent number
US07129208B2

Reaction notes

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