N-(tert-butoxycarbonyl)glycine → HCID 13503181, compound

HRID 371357Notes

Reaction equation

HRID 371357 reaction equation
[NH:1]([C:31]([O:33]CC1C=CC=CC=1)=O)[C@H:2]([C:15]([NH:17][C@H:18]([C:27]([O:29][CH3:30])=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:16])[CH2:3][C:4](=[O:14])[O:5]C(C1C=CC=CC=1)=O.[NH:41]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42]C(O)=O>CO.Cl.[Pd].[C]>[NH:41]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][C:31]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:27]([O:29][CH3:30])=[O:28])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)=[O:16])[CH2:3][C:4](=[O:14])[OH:5])=[O:33]

Participants

6

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 131714285HCID 131714285, compound

Product 1

HCID 13503181HCID 13503181, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

4.81 g (0.009 mole) of Z-Asp(OBz)-Tyr-OMe [m.p. 126°-127° C. [α]D24 =-4.8° (C=1, methanol). Anal. Calcd. (%) for C29H30N2O8 : C, 65.16; H, 5.66; N, 5.24. Found (%): C, 65.14; H, 5.71; N, 5.18] was dissolved in a mixture of 150 ml of methanol and 9 ml of 1N HCl and hydrogenated over 0.9 g of a 10% Pd-carbon catalyst at room temperature for 6 hours. Then the catalyst was filtered off, and the filtrate was distilled in vacuo to dryness. The resulting dipeptide was condensed with a mixed anhydride which had been prepared from 1.89 g of Boc-Gly-OH in the same manner as in (1) of Example 2. The product was recrystallized from ethyl acetate-ether, giving 3.09 g of Boc-Gly-Asp-Tyr-OMe; yield 71.8%, m.p. 97°-99° C.

Workup

  1. filtrationThen the catalyst was filtered off
  2. distillationthe filtrate was distilled in vacuo to dryness
  3. customcondensed with a mixed anhydride which
  4. customThe product was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-b7d14543ea044313907a513fdf284adf
Source dataset
uspto-grants-1985_07
Patent number
US04530836

Reaction notes

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