4-Methylmorpholine → HCID 57006984, compound

HRID 617896Notes

Reaction equation

HRID 617896 reaction equation
[CH2:1]([CH:8]([O:10][P:11]([CH2:14]C1(C(O)=O)CCCC1)([OH:13])=[O:12])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:25]1=[O:43].CN1CCOCC1.[OH:51][C:52]1[C:60]2N=NN[C:56]=2[CH:55]=[CH:54][CH:53]=1.Cl.CN(C)CCCN=C=NCC>>[CH2:1]([CH:8]([O:10][P:11]([CH2:14][N:23]([C:52]([CH:60]1[CH2:56][CH2:55][CH2:54][CH2:53]1)=[O:51])[C@H:24]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]([CH2:35][C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[C:25]1=[O:43])([OH:13])=[O:12])[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 63506241,1-Dimethylethyl ((3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetateHCID 53886611HCID 53886611, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 57006984HCID 57006984, compoundYield 29.3%

Procedure

5.0 g of 1-benzylethylphosphonomethyl-1-cyclopentanecarboxylic acid (preparation see Example 3E)) were reacted with 5.15 g of tert-butyl (3S)-3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation see Example 1E)), 4.1 ml of N-methylmorpholine, 2.0 g of hydroxybenzotriazole and 6.3 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride according to the method described in Example 1G). The resulting crude product was chromatographed on 200 g of silica gel (eluent: first n-hexane/ethyl acetate 1:1, then pure ester). 2.6 g of the title compound were obtained as a foamed resin, IR=3410, 3350, 1735, 1655 cm-1 ; [α]D20 =-118.1° (c=0.609 in methanol).

Workup

  1. customThe resulting crude product was chromatographed on 200 g of silica gel (eluent

Sources & evidence

ORD record
ord-7ff2e6463d0f4327a5acb92ed43c5266
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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