N-Naphthalen-2-ylalanine → HCID 59159247, compound

HRID 1096279Notes

Reaction equation

HRID 1096279 reaction equation
C1C2C(=CC=CC=2)C=CC=1NC(C)C(O)=O.COC(OC)CNCCCN1CCC2(CC2)[C@H](O)C1.CO[CH:38](OC)[CH2:39][N:40]([CH2:56][CH2:57][CH2:58][N:59]1[CH2:66][CH2:65][C:62]2([CH2:64][CH2:63]2)[C@H:61]([OH:67])[CH2:60]1)[C:41](=[O:55])[CH:42]([NH:44][C:45]1[CH:54]=[CH:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=1)[CH3:43]>>[OH:67][C@@H:61]1[CH2:60][N:59]([CH2:58][CH2:57][CH2:56][N:40]2[CH2:39][CH2:38][N:44]([C:45]3[CH:54]=[CH:53][C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:46]=3)[C@@H:42]([CH3:43])[C:41]2=[O:55])[CH2:66][CH2:65][C:62]21[CH2:64][CH2:63]2

Participants

4

Reactant 3

HCID 14535060N-Naphthalen-2-ylalanine2×HCID 66783066HCID 66783066, compoundHCID 66783309HCID 66783309, compound

Product 1

HCID 59159247HCID 59159247, compound

Procedure

The title compound was produced in analogy with examples 74 and 75, steps D-F. Thus, coupling of 2-(naphthalen-2-ylamino)-propionic acid (intermediate 16) with (S)-6-[3-(2,2-dimethoxy-ethylamino)-propyl]-6-aza-spiro[2.5]octan-4-ol (examples 74/75C) in step D led to N-(2,2-dimethoxy-ethyl)-N-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-(naphthalen-2-ylamino)-propionamide, which was cyclized in step E. Finally, HPLC purification of the epimeric mixture, 1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-3-methyl-4-naphthalen-2-yl-piperazin-2-one, in step F afforded the title compound. Light yellow gum, MS: 408.4 (M+H)+.

Workup

  1. customFinally, HPLC purification of the epimeric mixture, 1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-3-methyl-4-naphthalen-2-yl-piperazin-2-one

Sources & evidence

ORD record
ord-079f7f422b6c4b4989a126e36c0ca054
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

Loading…