Tert-butoxycarbonylalanine → HCID 13079748, compound

HRID 2295326Notes

Reaction equation

HRID 2295326 reaction equation
Cl.C(N=C=NCCCN(C)C)C.Cl.NCC(N[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C(O)C)C1)=O.[NH2:41][C@@H:42]1[CH2:61][CH2:60][C@@:59]2([CH3:62])[C@@H:44]([CH2:45][CH2:46][C@@H:47]3[C@@H:58]2[CH2:57][CH2:56][C@@:55]2([CH3:63])[C@H:48]3[CH2:49][CH2:50][C@@H:51]2[CH:52]([OH:54])[CH3:53])[CH2:43]1.[C:64]([NH:71][C@H:72]([C:74](O)=[O:75])[CH3:73])([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:69][C:67]([CH3:70])([O:66][C:64]([NH:71][CH:72]([CH3:73])[C:74]([NH:41][C@@H:42]1[CH2:61][CH2:60][C@@:59]2([CH3:62])[C@@H:44]([CH2:45][CH2:46][C@@H:47]3[C@@H:58]2[CH2:57][CH2:56][C@@:55]2([CH3:63])[C@H:48]3[CH2:49][CH2:50][C@@H:51]2[C@@H:52]([OH:54])[CH3:53])[CH2:43]1)=[O:75])=[O:65])[CH3:68]

Participants

7

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 22825173HCID 22825173, compoundHCID 70524041HCID 70524041, compound

Product 1

HCID 13079748HCID 13079748, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

1.14 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added with stirring under an inert atmosphere at 0° to 5° C. to a solution of 1.92 g of (20S) 3α-amino-5α-pregnan-20-ol, 2.27 g of tert.-butyloxycarbonyl-L-alaine (BOC-L-Alanine), 60 ml of chloroform and 12 ml of pyridine and the mixture was stirred for 75 minutes after which another 1.15 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added thereto. The mixture was stirred at 0° to 5° C. for 50 minutes and was evaporated to dryness. The residue was taken up in aqueous sodium bicarbonate solution and the solution was extracted with ethyl acetate. The organic phase was washed with aqueous saturated sodium chloride and then with aqueous N hydrochloric acid and then with aqueous saturated sodium chloride solution, dried and evaporated to dryness. The residue was crystallized from isopropyl ether and was vacuum filtered. The product was rinsed with isopropyl ether and dried at 60° C. under reduced pressure to obtain 2-[1,1-dimethylethoxycarbonylamino]-N-[(20S)-5α-pregnan-20-ol-3α-yl]-propanamide melting at 171° C.

Workup

  1. additionwas added
  2. customwas evaporated to dryness
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic phase was washed with aqueous saturated sodium chloride
  5. dry with materialwith aqueous N hydrochloric acid and then with aqueous saturated sodium chloride solution, dried
  6. customevaporated to dryness
  7. customThe residue was crystallized from isopropyl ether
  8. filtrationfiltered
  9. washThe product was rinsed with isopropyl ether
  10. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-14b1baef73a9457e9ed7271541900206
Source dataset
uspto-grants-1984_01
Patent number
US04424218

Reaction notes

Loading…