Acetic Acid → HCID 67415049, compound

HRID 2389103Notes

Reaction equation

HRID 2389103 reaction equation
[P:1]([O:5][CH2:6][C@:7]([NH:31]C(=O)OC(C)(C)C)([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH:20]3[CH2:25][CH2:24][C:23]4([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:22][CH2:21]3)[CH:15]=2)[CH:10]=1)[CH3:8])([OH:4])([OH:3])=[O:2].C(O)(=O)C.Cl>O>[P:1]([OH:3])([OH:4])([O:5][CH2:6][C@:7]([NH2:31])([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH:20]3[CH2:21][CH2:22][C:23]4([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)[CH2:24][CH2:25]3)[CH:15]=2)[CH:10]=1)[CH3:8])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 86642892HCID 86642892, compound

Product 1

HCID 67415049HCID 67415049, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl (2R)-1-(phosphonooxy)-2-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)propan-2-ylcarbamate (13.6 mg, 0.0000248 mol) was dissolved in acetic acid (0.78 mL, 0.014 mol) and 10 M of hydrogen chloride in water (0.2 mL) was added and the mixture was stirred for Id. Lypholyzing gave (2R)-2-amino-2-(6-(spiro[5.5]undecan-3-yloxy)naphthalen-2-yl)propyl dihydrogen phosphate as a white solid (4.0 mg, 36%). LCMS give a single peak Rf=1.64 min (431.41, [M-16]+, 100%, 895.73, [M+M+1], 20%). 1H NMR (400 MHz, MeOD) δ=7.82-7.89 (m, 3 H), 7.56 (d, J=5.5 Hz, 1 H), 7.27 (s, 1 H), 7.21 (d, J=8.6 Hz, 1 H), 4.54-4.47 (m, 1 H), 4.14-4.17 (m, 2H), 1.99-1.90 (m, 2 H), 1.86 (s, 3 H), 1.78-1.66 (m, 4 H), 1.50 (m, 8 H), 1.42-1.30 (m, 4 H).

Sources & evidence

ORD record
ord-cf1bd3a94e4f493785890c9f491b4b20
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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