Ethylmorpholine → HCID 13178807, compound

HRID 1154158Notes

Reaction equation

C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:24][C@H:25]([C:36]([N:38]1[CH2:49][CH2:48][CH2:47][C@H:39]1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1.Cl.[NH:51]([C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C@@H:52]([C:60](O)=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:51]([C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C@@H:52]([C:60]([NH:24][C@H:25]([C:36]([N:38]1[CH2:49][CH2:48][CH2:47][C@H:39]1[C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41])=[O:37])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=[O:61])[CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.28 ml (10 mmoles) of N-ethylmorpholine and 2.26 g (11 mmoles) of DCC are added at 0° C. to a solution of 3.46 g (10 mmoles) of H-Trp-Pro-OBut.HCl. 2.29 g (10 mmoles) of Z-D-Phe-OH and 1.35 g (10 mmoles) of HOBt in 25 ml of dimethylformamide. The mixture is stirred for 2 hours at 0° C. and left to stand overnight at room temperature. The precipitate is filtered and the filtrate is concentrated. The residue is worked up analogously to Example 1 a. The residue crystallizes from ether. Yield 3.91 g (61%), melting point 186°, [α]D23 =-53.6° (c=1, methanol).

Workup

waitleft
waitto stand overnight at room temperature
filtrationThe precipitate is filtered
concentrationthe filtrate is concentrated
customThe residue crystallizes from ether
customYield 3.91 g (61%), melting point 186°, [α]D23 =-53.6° (c=1, methanol)

Sources & evidence

ORD record: ord-8b0894fd8b2a43a49dc6d61d882724cc
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04487764

Reaction notes

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