Diethylamine → methyl (1S)-1-({[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

HRID 1174114Notes

Reaction equation

[CH2:1]([C@H:8]([NH:38][C:39]([C@@H:41]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:9][C@H:10]([OH:37])[C@@H:11]([NH:19]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NCC)C>CN(C=O)C>[NH2:19][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@@H:10]([OH:37])[CH2:9][C@@H:8]([NH:38][C:39]([C@@H:41]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 3C (0.130 g, 0.192 mmol) in DMF (6 mL) was treated with diethylamine (1.5 mL), stirred at 25° C. for 1 hour, and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with a gradient starting with ethyl acetate and ending with methanol to give the title compound (0.52 g, 60% yield).

Workup

custompartitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with a gradient

Sources & evidence

ORD record: ord-0db22f7bfa3046dcb7fc4088a648bd36
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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