1,2-Dichloroethane → HCID 53863499, compound

HRID 1902162Notes

Reaction equation

CC(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:14]2)[CH2:10][CH2:9]1)=O)(C)C.Cl.[CH3:29][C:30]([CH3:49])([O:32][C:33]([NH:35][C@H:36]([CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]([OH:39])=O)=[O:34])[CH3:31].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>>[CH3:49][C:30]([O:32][C:33](=[O:34])[NH:35][CH:36]([C:37]([N:8]1[CH2:9][CH2:10][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:14]2)[CH2:12][CH2:13]1)=[O:39])[CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([CH3:29])[CH3:31]

Participants

Reactant 6

HCID 111,2-Dichloroethane

HCID 313Hydrochloric Acid

HCID 79724-Methylmorpholine

HCID 757711-Hydroxybenzotriazole

HCID 7016821(R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid

HCID 54470166HCID 54470166, compound

Product 1

HCID 53863499HCID 53863499, compoundYield 69.7%

Procedure

The intermediate from Step A (120 mg, 0.33 1 mmol) was treated with 4N HCl as in Example 85, Step A. The residue was reacted with the compound prepared in Example 73, Step B (97 mg, 0.33 mmol), EDC (94.7 mg. 0.496 mmol), HOBT (67 mg, 0.49 mmol) and NMM (0.076 ml, 0.66 mmol) according to the procedure described for Example 1, Step A. The title compound (123 mg, 0.23 mmol) was obtained as a white solid after flash chromatography.

Sources & evidence

ORD record: ord-3b6a8d27ad7a4b89a4434850c1e6b7f6
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578593

Reaction notes

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