Dicyclohexylcarbodiimide → HCID 53845728, compound

HRID 345903Notes

Reaction equation

Cl.CO.[NH:4]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:5]([C:13](N[C@H](C(O)=O)CC1N=CNC=1)=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.ON1C2C=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.[CH:43]1(N=C=NC2CCCCC2)CCCCC1>>[C:29]([O:28][C:26]([NH:4][C@H:5]([CH:13]=[CH:40][CH2:41][CH:42]([CH3:37])[CH3:43])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 21893726Hydrochloride methanol

HCID 178454152HCID 178454152, compound

Product 1

HCID 53845728HCID 53845728, compoundYield 40%

Procedure

The 3(R),4(S) diastereomer of Example 5d was deprotected with HCl/methanol, and the resulting product was coupled to Boc-Phe-His using 1-hydroxybenzotriazole and 1,3-dicyclohexylcarbodiimide according to the procedure of Example 5b. The desired product was obtained in 40-60% yield, Mass spectrum: (M+H)+ =628.

Sources & evidence

ORD record: ord-a19f238975c740279ca0199139f32a7c
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05059589

Reaction notes

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