Hydrochloric Acid → HCID 131716521, compound

HRID 1709963Notes

Reaction equation

HRID 1709963 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22](O)=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:32][C@H:33]([C:39]([OH:41])=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37].Cl>CN(C=O)C>[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([NH:32][C@H:33]([C:39]([OH:41])=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5961L-Glutamine2×HCID 131716517HCID 131716517, compound

Product 1

HCID 131716521HCID 131716521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Phe-Gly-Leu-Gln-NA was prepared by coupling Boc-Phe-Gly-Leu-OH (1.42 g, 3.25 mmol) to H-Gln-NA HCl (1.00 g, 3.25 mmol) by a mixed anhydride coupling procedure. A total of 10 mL DMF was used to dissolve H-Gln-NA HCl. During workup of the organic phase resulting from the mixed anhydride coupling procedure, some product crystallized and was separated, washed with water, and dried to yield 0.91 g of Boc-Phe-Gly-Leu-Gln-NA, mp 238°-239°. The remaining organic phase was washed with a saturated salt solution, and a second crop of crystalline product (0.62 g) was obtained, mp 238°-239°. A sample of the first crop was analyzed.

Sources & evidence

ORD record
ord-2dde0f9f10e8492fa83ca0c42bc6800c
Source dataset
uspto-grants-1990_08
Patent number
US04952493

Reaction notes

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