Hydrochloric Acid → HCID 131711927, compound

HRID 904045Notes

Reaction equation

HRID 904045 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:55]([NH:57][C@H:58]([C:61]([NH:63][C@H:64]([C:69]([O:71]C(C)(C)C)=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[CH2:59][OH:60])=[O:56])[CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)=[O:13])[CH3:11])=[O:8].FC(F)(F)C(O)=O.Cl.N[C@H](C(O)=O)CCCCN.N[C@H](C(O)=O)CC(=O)O.N[C@H](C(O)=O)CCC(=O)O.NCC(O)=O.N[C@H](C(O)=O)C.N[C@H](C(O)=O)CC(C)C>O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:55]([NH:57][C@H:58]([C:61]([NH:63][C@H:64]([C:69]([OH:71])=[O:70])[CH2:65][C:66](=[O:68])[NH2:67])=[O:62])[CH2:59][OH:60])=[O:56])[CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[O:13])[CH3:11])=[O:8]

Participants

11

Reactant 9

HCID 313Hydrochloric AcidHCID 750GlycineHCID 5950L-AlanineHCID 5960L-Aspartic AcidHCID 5962L-LysineHCID 6106L-LeucineHCID 6422Trifluoroacetic acidHCID 33032L-Glutamic AcidHCID 131711928HCID 131711928, compound

Product 1

HCID 131711927HCID 131711927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

450 mg of pGlu-Ala-Lys(Boc)-Ser-Gln-Gly-(D)-Leu-Ser-Asn-OBut is treated with 5 ml of trifluoroacetic acid at room temperature for 40 minutes and the reaction product is purified as in Example 1-(VIII). Yield 260 mg (58%); [α]D23 -40.0° (c=0.31, H2O); Rf4 (Avicel)=0.23, amino acid analysis (hydrolyzed with HCl); Lys, 0.95(1); Asp, 0.92(1); Ser, 1.79(2); Glu, 2.05(2); Gly, 1.01(1); Ala, 1.05(1); Leu, 1.05(1); average recovery 81%.

Sources & evidence

ORD record
ord-88d09238ae384febab6b63b24a820783
Source dataset
uspto-grants-1980_10
Patent number
US04229438

Reaction notes

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