Hydrochloric Acid → N-But-2-en-1-ylglycine

HRID 494909

반응식

HRID 494909 반응식
C(O[N:19]1[C:24](=O)[CH2:23][CH2:22][C:20]1=O)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.Cl.N[C@@H:28](CC=CC)[C:29]([OH:31])=[O:30].C([O-])(O)=O.[Na+].Cl>CC(C)=O.O>[CH2:24]([NH:19][CH2:28][C:29]([OH:31])=[O:30])[CH:23]=[CH:22][CH3:20]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 131727453(2s)-2-Aminohex-4-enoic acid hydrochloride salt

생성물 1

HCID 53407996N-But-2-en-1-ylglycine수율 211.3%

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

2-N-Fluorenylmethoxycarbonylaminohex-4-enoic acid 100 was prepared according to the procedure described by Paquet.230 Fmoc-OSu (2.36 g, 7.00 mmol) was added to a stirred suspension of L-crotylglycine HCl 101 (1.16 g, 7.03 mmol) and NaHCO3 (2.95 g, 35.0 mmol) in a mixture of acetone:water (1:1, 30 mL). The resultant suspension was stirred at room temperature for 15 h. The reaction mixture was then acidified with concentrated HCl (pH 2) and the acetone was removed under reduced pressure. The resultant suspension was extracted into DCM (3×25 mL) and the combined organic extract was washed with dilute HCl solution (1 M, 2×25 mL), water (2×25 mL), dried (MgSO4) and evaporated under reduced pressure to afford the titled Fmoc-amino acid 100 as colourless solid (1.91 g, 78%), m.p. 119-121° C. νmax (KBr): 3390 bm, 3033 m, 2961 s, 2357 w, 1730 s, 1651 w, 1505 w, 1450 w, 1395 w, 850 w cm−1. 1H n.m.r. (300 MHz, CDCl3): δ 1.67 (d, J=6.2 Hz, 3H, H6), 2.37-2.69 (m, 2H, H3), 4.23 (t, J=6.8 Hz, 1H, H9′), 4.42-4.48 (m, 3H, CH2O, H2), 5.30-5,37 (m, 2H, H5, NH), 5.61 (m, 1H, H4), 7.31 (td, J=7.2, 1.3 Hz, 2H, H2′, 7′), 7.34 (td, J=7.4, 1.5 Hz, 2H, H3′, 6′), 7.60 (d, J=7.3 Hz, 2H, H1′, 8′), 7.74 (d, J=7.0 Hz, 2H, H4′, 5′), one exchangeable proton (OH) not observed. 13C n.m.r. (75 MHz, CDCl3): δ 16.7 (C6), 34.1 (C3), 46.2 (C9′), 52.3 (C2), 66.2 (CH2O), 118.9 (C5), 123.0 (C2′, 7′), 124.6 (C3′, 6′), 125.2 (C1′, 8′), 127.5 (C4′, 5′), 129.7 (C4), 140.3 (C8′a, 9′a), 142.7 (C4′a, 4′b), 154.9 (OCONH), 175.0 (C1). Mass Spectrum (ESI+, MeOH): m/z 352.1 (M+H)+, C21H22NO4 requires 352.2. Spectroscopic data were in agreement with those reported in the literature.146

후처리

  1. custom2-N-Fluorenylmethoxycarbonylaminohex-4-enoic acid 100 was prepared
  2. customthe acetone was removed under reduced pressure
  3. extractionThe resultant suspension was extracted into DCM (3×25 mL)
  4. extractionthe combined organic extract
  5. washwas washed with dilute HCl solution (1 M, 2×25 mL), water (2×25 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d87eba1ac6fd4e388095fa4aff2837b9
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538190B2

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